3 Bedroom

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3 Bedroom
Welcome to Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous and breath-taking views. Simply walk downstairs, and cross over to arrive at our most cherished and sought after beach in the world. This is your backyard... welcome to Paradise!

Admirals Watch not only has the best views of all of Siesta Key, but it also features a spacious living area, open and and inviting with endless views from the kitchen, dining, and living room. The bedrooms are tucked privately away, with dual master suites featuring private bathrooms and king beds (sleeps 2 in each master room). The guest room features a trundle bed (sleeps 2) with a semi-private bathroom en suite. The home comfortably sleeps 8 with a plush twin sofa sleeper in the upstairs loft along with additional space for an airbed should you choose to bring one (sleeps 2).

Admirals Watch has one of the finest kitchens that even a professional chef would enjoy! Fully stocked, and ready to accommodate a large gathering, the chef can partake in the festivities of the party thanks to the open and spacious floorplan, all the while guests can belly up to the kitchen bar for great conversation and libations! Top of the line stainless steel appliances, granite counters, and gorgeous and spacious cabinets reminds you that this home is nothing short of luxurious.

Just downstairs (and feel free to take the stairs or the private elevator), a world of fun opens up to you and your friends and family, with the best amenities available to you as part of your stay! In the garage, you will find all the great beach gear that you need for an easy trek across the road to the finest and coolest powdered sand beach the world has to offer. A beach caddy that holds your chairs, towels, and cooler are standing by to make the stroll that much easier. When it's time to explore the island, why not hop on your beach cruisers, and head to Siesta Key Village... only just a few moments away. The walk to the village is just as easy! It's just around the corner, and you can be there in less than 10 minutes. And when you've decided it's time to head back from a long day at the beach, plan your evening in by hopping in the heated swimming pool and treating the family to the perfect BBQ dinner on the gas grill! Plenty of loungers and seating options make it easy for the whole family to gather for a feast!

Siesta Key Village offers the best dining and entertainment, and you're just moments away from all that makes Siesta Key fabulous! The location is perfect! The beach, the village, the views.... none of which can be beat! Welcome to your next vacation home, Admirals Watch!

 
 


 
Bedrooms3
Bathrooms3
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $315
Price Per Weekfrom $2200
3 Bedroom
Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous and breath-taking views. Simply walk downstairs, and cross over to arrive at our most cherished and sought after beach in the world. This is your backyard... welcome to Paradise!

Villa Vista Mare not only has the best views of all of Siesta Key, but it also features a spacious living area, open and inviting with endless views from the kitchen, dining, and living area. The bedrooms are tucked privately away, with a queen bed (sleeps 2) in the master and a trundle bed (sleeps 2) in the second guest room. The third guest room features a queen bed (sleeps 2). The home comfortably sleeps 8 with a plush sofa sleeper for two in the living area.

Villa Vista Mare has one of the finest kitchens that even a professional chef would enjoy! Fully stocked, and ready to accommodate a large gathering, the chef can partake in the festivities of the party thanks to the open and spacious floorplan, all the while guests can belly up to the kitchen bar for great conversation and libations! Top of the line stainless steel appliances, granite counters, and gorgeous and spacious cabinets reminds you that this home is nothing short of luxurious.

Just downstairs (and feel free to take the stairs or the private elevator), a world of fun opens up to you and your friends and family, with the best amenities available to you as part of your stay! In the garage, you will find all the great beach gear that you need for an easy trek across the road to the finest and coolest powdered sand beach the world has to offer. A beach caddy that holds your chairs, towels, and cooler are standing by to make the stroll that much easier. When it's time to explore the island, why not hop on your beach cruisers, and head to Siesta Key Village... only just a few moments away. The walk to the village is just as easy! It's just around the corner, and you can be there in less than 10 minutes. And when you've decided it's time to head back from a long day at the beach, plan your evening in by hopping in the heated swimming pool and treating the family to the perfect BBQ dinner on the gas grill! Plenty of loungers and seating options make it easy for the whole family to gather for a feast!

Siesta Key Village offers the best dining and entertainment, and you're just moments away from all that makes Siesta Key fabulous! The location is perfect! The beach, the village, the views.... none of which can be beat! Welcome to your next vacation home, Villa Vista Mare!


Bedrooms3
Bathrooms3
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $295
Price Per Weekfrom $2000
3 Bedroom
Situated on the northern part of Siesta Key within walking distance to Nora Patterson’s Park, this original Sarasota home is tucked within the Bay Island! With just a short drive to main beach access parking and even closer to the shops both on the Key and off, this location is the perfect setting for the family moments and the adventures you can experience whether you like to jog, bike or simply explore your own way!

Endearingly engaging once you walk through the door, you are whisked away into a sweeping living and dining area, spacious family-style kitchen all with views to the outdoor screened-in lanai and seating area, heated pool and grassy knoll.

From the living room with an L-shaped couch that will encompass you, to the dining area with ample seating for six (6), you are always within view of the tri-sliding doors that open to provide easy access to the best moments of the day poolside! We would be remiss if we didn’t note the timeless lighting touches throughout the property, which always you to selectively light (dim or brighten) the home at your desire. It might sound strange to note, but there is nothing like an old-world glow in the corner while you daydream and indulge the night away.

Nothing says sunny days then an almost endless countertop in the kitchen, space to leave out the necessities, munchies, and beverages while providing room for meal preparation! With open space shelving, textured back walls and the latest Whirlpool stainless steel appliances (convection oven, glass cooktop, double door refrigerator, and dishwasher), you will feel the freedom the space provides!

The screened-in pool deck has multiple seating areas with the indoor/outdoor kitchen bar area that makes the perfect place to belly up to the window to pass food and beverages from the kitchen to poolside. There is a relaxing light in the far corner on the lanai for those after dinner swims and late-night shenanigans!

For the younger travelers, there is no better place to bunk together then this bungalow’s kids room. Light-hearted, with a single top bunk, double bed on bottom and a single trundle pull-out, vacation slumber parties have never been so much fun.

With two additional bedrooms, each with a king bed and one with a private bathroom, you will find yourself tossing a coin to figure out which of you enjoys the pool view! Eloquently appointed and refinished bathrooms are joined via brand new beach wood tile floors. Window shades will help you ease into the day for the late night warriors or afternoon nappers. We have all been known to take a snooze after a day at the beach and prepare for an evening of fun.

Take your shoes off the moment you walk through the door and feel the textures, the breeze, the sun… Welcome to Baydream Bungalow!


Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Weekfrom $1250
3 Bedroom
Welcome to Monarch Villa! The luxurious three (3) bedroom, three (3) bathroom townhome features a heated pool and panoramic views of the Gulf. With panoramic views and refreshing sea breezes, you'll be living the dream in this Siesta Key vacation home. Enjoy the absolute BEST location only a moment's walk to the Siesta Key Village. Monarch Villa is lovingly cared for... the amenities and details put into each room take into consideration what every guest desires to make the perfect vacation setting.

Enjoy a master with a king size bed (sleeps 2), a guest room featuring a king size bed (sleeps 2), and a third guest room that features two twin beds (sleeps 2). Additionally, enjoy the comforts of extra sleeping arrangements for two with a pull out sofa sleeper (sleeps 2). This home comfortably sleeps 8 with fine bedding and linens. The kitchen is well-equipped for the chef in the family to enjoy cooking large meals all the while mingling with their family and guests in the open living room and dining room area.

When it's time to BBQ on the grill, just step out to your poolside (shared with Peacock Villa) and feel free to bask in the sunshine with loungers, or cozy up to a table under an umbrella for shade. Don't forget you have your very own private poolside cabana equipped with an HDTV, comfortable couches and seating, fully air conditioned for your maximum comfort. There is something here for everyone to enjoy!

Please note: this property has an elevator for easy access to all floors.
Bedrooms3
Bathrooms3
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $215
Price Per Weekfrom $1500
3 Bedroom
Welcome to Peacock Villa! The luxurious three (3) bedroom, three (3) bathroom townhome features a heated pool and panoramic views of the Gulf. With panoramic views and refreshing sea breezes, you'll be living the dream in this Siesta Key vacation home. Enjoy the absolute BEST location only a moment's walk to the Siesta Key Village. Peacock Villa is lovingly cared for... the amenities and details put into each room take into consideration what every guest desires to make the perfect vacation setting.

Enjoy a master with a king size bed (sleeps 2), a guest room featuring a king size bed (sleeps 2), and a third guest room that features two twin beds (sleeps 2). Additionally, enjoy the comforts of extra sleeping arrangements for two with a pull out sofa sleeper (sleeps 2). This home comfortably sleeps 8 with fine bedding and linens. The kitchen is well-equipped for the chef in the family to enjoy cooking large meals all the while mingling with their family and guests in the open living room and dining room area.

When it's time to BBQ on the grill, just step out to your poolside (shared with Monarch Villa) and feel free to bask in the sunshine with loungers, or cozy up to a table under an umbrella for shade. Don't forget you have your very own private poolside cabana equipped with an HDTV, comfortable couches and seating, fully air conditioned for your maximum comfort. There is something here for everyone to enjoy!

Please note: this property has an elevator for easy access to all floors.
Bedrooms3
Bathrooms3
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $215
Price Per Weekfrom $1400
3 Bedroom
Welcome to CocoBayou Cottage!


Please Note:
Sleeps 10: 3K, 2SS
The units [Casita Bayou & Casita Coco] are rented together.
When combined, these units are called: CoCoBayou Cottage (Sleeps 10)
If one property is not available, please contact us for the availability of another comparable property!


This uniquely configured private home is the perfect escape with lots of charm and is conveniently located to Crescent Village and the south bridge into Sarasota. This gorgeous beachy getaway comfortably sleeps 10 in beds with fresh linens. The property has recently been updated with stylish furnishings and is completely renovated to include a BRAND NEW heated pool in the backyard!


The 3BR/ 2BA spacious floor plan includes 2 king beds and a sofa sleeper in one unit [Casita Bayou] and 1 king and sofa sleeper in the other unit [Casita Coco], making this home roomy enough for everyone. You’ll enjoy both a fully equipped kitchen and washer/dryer for each unit (no waiting turns to do laundry with a large group) thank goodness! There are three sitting/living rooms, beautiful landscaping, an outdoor shower, plenty of lounge chairs for basking in the sun, and all the beach towels you could need. Both patios have a grill for dining and entertaining by the private pool, as well as patio dining tables to enjoy the fresh air (Casita Bayou’s patio is screened in)! We’ve provided colorful beach chairs, bicycles, and propane for the gas grills for your convenience. If you want to stay connected there are 5 flat screen TVs, cable television, free Wi-Fi, and a telephone.


CocoBayou Cottage is in one of the most cherished locations on Siesta Key! Just one block from Crescent Village and tucked into a quaint neighborhood that offers the best of all worlds, Siesta Key's world famous beach is only a 5 minute walk west, and there's also the option of taking the kayaks to the Intracoastal for an absolutely phenomenal tour of the bay! Dolphins, fish and birds are abound everywhere, making the experience unforgettable. In the evenings, walk to the village for some excellent restaurants, bars and shopping!
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $225
Price Per Weekfrom $1400
3 Bedroom
Baybreeze is one-half of the beautiful "Coconut Grove," a large home that has the unique capability of renting as two separate units or combined for larger families. Baybreeze is the upper unit of "Coconut Grove" and "Pinacolada" is the lower unit. Please note there are stairs to access Baybreeze. Each unit boasts three bedrooms and three bathrooms. When combined "Baybreeze" and "Pinacolada" can create a perfect sense of space between being under one roof and yet plenty of separation for times of self-indulgence. Inspired by island living, this beautiful retreat embodies relaxation and peace of mind. Tucked behind the village, it gives just enough privacy to make you feel you are in your own haven of serenity, but step outside and be right in the midst of America's #1 Beach and the village surrounding it. And what more could you want other than beaches, beaches and more beaches!!! How about the fact that everything is in walking distance! From restaurants, bars, shopping, and entertainment, it encompasses all things that make a vacation great! There is always live music and fresh seafood waiting for you, your family and friends right around every corner! Being this close to the beach means a quick stroll over to the best part of Siesta- we even provide beach caddies, chairs, and towels to make it that much more achievable and relaxing. Meander on foot and feel the soft sugary sand under your feet in less than 3 minutes, or hop on the free trolleys provided and take a day excursion exploring the village and the cool sandy beaches from north to south.

Baybreeze features a semi-private heated pool (it shares access with only its sister unit, "Pinacolada"), a gas grill, privately enclosed pool area, a view of Siesta Key Village and many other great amenities to make your daily adventures more fun than ever. Inside, the home is outfitted with an open kitchen and living room floorplan, making it ideal to entertain many guests at once. Inside, you will find the master features a king size bed and a private bathroom. The two guest rooms feature 1 queen in the first and two queens in the second. There is a shared guest bathroom for the guest rooms and a half bath nearest to the living area. The home comfortably sleeps 8 altogether.

Baybreeze is luxurious in every sense of the word. Plush bedding and pillows, HDTVs in all the bedrooms and the living room, balconies extending from the living room and kitchen areas and a staircase from the top unit leading down to the tranquil pool area. Grab a beverage or two, and head down to the poolside to grill out for a private evening under the stars. Kick back and listen to the sounds of Siesta as night descends. Being in the heart of it all makes Siesta Key that much more amazing in every way. Embrace love, laughter, and happiness on your vacation right here, inspired by the beauty of Siesta Key!


Bedrooms3
Bathrooms2.5
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $210
Price Per Weekfrom $1300
3 Bedroom
Welcome to Pinacolada! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 8, a shared heated pool, and quite literally in the heart of Siesta Village!

Pinacolada is one-half of the exquisite "Coconut Grove," a large home that has the unique capability of renting as two separate units or combined for larger families. Pinacolada is the lower unit of "Coconut Grove" and "Baybreeze" is the upper unit. Each unit boasts three bedrooms and 2.5 bathrooms. When combined "Pinacolada" and "Baybreeze" can create a perfect sense of space between being under one roof and yet plenty of separation for times of self-indulgence. Inspired by island living, this beautiful retreat embodies relaxation and peace of mind. Tucked behind the village, it gives just enough privacy to make you feel you are in your own haven of serenity, but step outside and be right in the midst of America's #1 Beach and the village surrounding it. And what more could you want other than beaches, beaches and more beaches!!! How about the fact that everything is in walking distance! From restaurants, bars, shopping, and entertainment, it encompasses all things that make a vacation great! There is always live music and fresh seafood waiting for you, your family and friends right around every corner! Being this close to the beach means a quick stroll over to the best part of Siesta- we even provide beach caddies, chairs, and towels to make it that much more achievable and relaxing. Meander on foot and feel the soft sugary sand under your feet in less than 3 minutes, or hop on the free trolleys provided and take a day excursion exploring the village and the cool sandy beaches from north to south.

Pinacolada features a semi-private heated pool (it shares access with only its sister unit, "Baybreeze"), a gas grill, privately enclosed pool area, a view of Siesta Key Village and many other great amenities to make your daily adventures more fun than ever. Inside, the home is outfitted with an open kitchen and living room floorplan, making it ideal to entertain many guests at once. Inside, you will find the master features a king size bed and a private bathroom. The two guest rooms feature 1 queen in the first and two queens in the second. There is a shared guest bathroom for the guest rooms and a half bath nearest to the living area. The home comfortably sleeps 8 altogether.

Pinacolada is luxurious in every sense of the word. Plush bedding and pillows, HDTVs in all the bedrooms and the living room, balconies extending from the living room and kitchen areas and a staircase from the top unit leading down to the tranquil pool area. Grab a beverage or two, and head down to the poolside to grill out for a private evening under the stars. Kick back and listen to the sounds of Siesta as night descends. Being in the heart of it all makes Siesta Key that much more amazing in every way. Embrace love, laughter, and happiness on your vacation right here, inspired by the beauty of Siesta Key!


Bedrooms3
Bathrooms2.5
Rental TypeCondo
Pet Friendly?
Price Per Nightfrom $210
Price Per Weekfrom $1300
3 Bedroom
Luna Nueva, a gorgeous 3 bedroom 2 bathroom villa located mid-town with easy access to Siesta Key - approximately less than 10 minutes away via car. All within walking distance you will find an amazing array of restaurants and shops in the immediate vicinity. Trader Joe's, an excellent supermarket is within 1 block and easy to walk. Luna Nueva is one of two special vacation homes that can be reserved separately or combined. The other available home is called Villa Las Flores and combined we call them Luna Flores.

Not only a great location, but 3 bedrooms fully furnished, each with wall-mounted HDTVs, ceiling fans. There are two bathrooms featuring slate floors, with expansive shower in one and a tub/shower configuration in the other, and beautiful cabinetry.The dining room seats 6 plus 4 at the bar counter. The kitchen features stainless steel equipment to include a refrigerator, microwave, stove/oven and a dishwasher. Every detail is driven by your gourmet chef's needs to include granite counters and a gooseneck sink faucet. There is a fully equipped laundry room off of the kitchen.

Outside, an exterior privacy fence surrounds your private and heated pool and has been entirely revised and replaced, along with an additional expansive courtyard paver area with lush landscaping and night lighting.

Welcome to your new vacation home rental, Luna Nueva! Contact our vacation specialists on how to reserve your space at the combined Luna Flores or separately as Luna Nueva or Villa Las Flores to suit your vacation needs.
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $132
Price Per Weekfrom $875
3 Bedroom
This inviting 3 bedroom/2 bathroom home features a private heated pool and is centrally located near downtown Sarasota. With just a short drive to world famous Siesta Key Beach, you will truly be living the Florida Life! Villa Las Flores is the ideal home for small families and couples looking for a tropical getaway.

Villa Las Flores can accommodate up to 8 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: Queen Bed (1) - Sleeps: 2
• Bedroom # 3: Twin Bed (2) - Sleeps: 2
• Living Room: Sleeper Sofa (1) - Sleeps: 2

Exclusive Amenities Include:

• Private Heated Pool
• Coffee Maker (Regular & Keurig)
• Outdoor Grill
• Linens Provided
• Kitchen Essentials Provided
• Wall-Mounted HDTVs + 1 in each bedroom
• Stainless Steel Appliances in Kitchen
• Granite Counters
• Dining Room (seats up to 6)
• Gooseneck Faucet (in kitchen)
• Privacy Fence
• Dishwasher
• Washer & Dryer
• Breakfast Counter
• Screened-In Seating Area
• Outdoor Lounging Area
• Outdoor Dining Area
• Free WiFi
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $132
Price Per Weekfrom $875
3 Bedroom
Welcome to the Sandy Cabana!

Please Note:
Sleeps 8- King, Queen, 2 Twins, Queen Air Bed
These units [Sandy Cabana & Seahorse Cabana] can be rented separately.
Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16)
If one unit is not available, please contact us for the availability of the other!


The Sandy Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous beachy getaway comfortably sleeps 6. The property has recently been updated with new furnishings, linens and more! If you need to stay connected there are 3 flat screen TVs, cable television, free WiFi, and a telephone.

This 3BR/ 2.5BA spacious floor plan includes a king bed [sleeps 2], a queen bed [sleeps 2], 2 twin beds [sleeps 1 each], and a queen air bed [sleeps 2] and can therefore accommodate up to 8 guests (6 Adults Maximum please). The kitchen comes fully equipped and you’ll enjoy an indoor stackable washer/ dryer, and a screened in private lanai. The pool is surrounded by tall pines, tropical palms, and blooming seasonal flowers for some shade and ambiance in addition to the lounge chairs and picnic tables with umbrellas to enjoy the Florida sun.

The location is exceptional, just a short 1.5 block walk to Point of the Rocks beach access and the beautiful white sands of Crescent Beach. No need to drive anywhere with less than a ¼ mile walk to great shops, bars, restaurants, a grocery store and drugstore all located in the South Village-Crescent Beach area.

If you have a larger party [up to 16] and would like to book the entire cottage [Sandy Cabana & Seahorse Cottage], you will need to reserve Sandy Seahorse Cottage, which consists of both units.
Bedrooms3
Bathrooms2.5
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $150
Price Per Weekfrom $1050
3 Bedroom
Welcome to the Seahorse Cabana!

Please Note:
Sleeps 8: King, Queen, 2 Twins, Queen Air Bed
These units [Sandy Cabana & Seahorse Cabana] can be rented separately.
Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16)
If one unit is not available, please contact us for the availability of the other!


The Seahorse Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous beachy getaway comfortably sleeps 6. The property has recently been updated with new furnishings, linens and more! If you need to stay connected there are 3 flat screen TVs, cable television, free Wi-Fi, and a telephone.

This 3BR/ 2.5BA spacious floor plan includes a king bed [sleeps 2], a queen bed [sleeps 2], 2 twin beds [sleeps 1 each], and a queen air bed [sleeps 2] and can therefore accommodate up to 8 guests (6 Adults Maximum please). The kitchen comes fully equipped and you’ll enjoy an indoor stackable washer/ dryer, and a screened in private lanai. The pool is surrounded by tall pines, tropical palms, and blooming seasonal flowers for some shade and ambiance in addition to the lounge chairs and picnic tables with umbrellas to enjoy the Florida sun.

The location is exceptional, just a short 1.5 block walk to Point of the Rocks beach access and the beautiful white sands of Crescent Beach. No need to drive anywhere with less than a ¼ mile walk to great shops, bars, restaurants, a grocery store and drugstore all located in the South Village-Crescent Beach area.

If you have a larger party [up to 16] and would like to book the entire cottage [Sandy Cabana & Seahorse Cottage], you will need to reserve Sandy Seahorse Cottage, which consists of both units.
Bedrooms3
Bathrooms2.5
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $150
Price Per Weekfrom $1050
3 Bedroom
Welcome to Serenity Cottage!

A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a delightful and relaxing retreat with maximum comforts in mind, and a spacious abode designed around the needs and comforts of large families traveling together!

Enjoy the delicate care that the owner has taken into making this home the absolute best option for their guests to come. The kitchen is meticulously designed for large families to come together and cook feasts with expansive cabinetry, upgraded stainless steel appliances, and plenty of counter space. Dining options are abundant for both inside and out, where just off the living room your family and friends can enjoy meals together under a sheltered screen-in lanai regardless of the weather. Sit back and relax in front of the extra large HD Flat TV in the living room, on soft and plush leather couches and decor pillows. The owner has created a desirable haven for revitalization, rejuvenation and serenity for the soul. And when you step out to the pool area, prepared to be invigorated by the warm glowing sun shining down on a pristine pool, cool for summers, and heated for the winters... Feel refreshed every day you wake by a quick dip in the refreshing waters of Serenity Cottage.

The bedrooms provide plush coziness and personal solace with new bedding, HDTVs in every room, providing everyone a space to call their own. The home comfortably sleeps 8 altogether, with the master featuring a king size bed (sleeps 2), a 2nd master that features a queen size bed (sleeps 2), and the children's room that features a unique bunk bed combination and trundle (sleep 4).

Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation of limestone rock that extends from the beach out into the Gulf of Mexico. This location has become home to a wide array of tropical fish and is not only a great environment for fishing but the only real location for great snorkeling on the Island.

Please Note:
If this unit is not available, please contact us for the availability of another comparable one!

We are certain that once you get here, you will never want to leave, but we are absolutely positive you will always return....
Bedrooms3
Bathrooms3.5
Rental TypeTownhome
Pet Friendly?
Price Per Nightfrom $193
Price Per Weekfrom $1350
3 Bedroom
This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? Siesta Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta offers a shared heated pool with its sister property Sea la Vie (when booking Siesta Salt Life, the pool is private). The kitchen features stainless steel appliances, a dining room table that fits up to 6, and a breakfast counter. The living area features a flat screen TV and access to the outdoor private patio. With plantation shutters and coastal décor throughout, you will truly feel the charm of Siesta Key living. Each bedroom features a flat screen TV & offers unique views of the home, from the outside pool area, to the lush jungle-like landscaping of the backyard. Step outside & you’ll find a massive outdoor area featuring a tranquil pool & BBQ area: perfect for family gatherings! The outside area also features a shower station. Book Sea Esta, and let your cares drift away. You Have Arrived…

Sea Esta can accommodate up to 8 guests, with a bedding configuration as follows:

• Bedroom 1: King Bed (1) – Sleeps: 2
• Bedroom 2: Queen Bed (1) -Sleeps: 2
• Bedroom 3: Queen Bed (2) – Sleeps 4

Exclusive Amenities Include:

• Close proximity to Siesta Key Public Beach (access # 7 is only 207 ft. away!)
• Walking distance to Siesta Key Village shops & restaurants
• Semi-Private Heated Pool (when combined with both units pool is private)
• Coffee Maker
• Stainless Steel Appliances
• Plantation Shutters
• Flat screen TV
• Flat Screen TVs in each bedroom
• Complimentary Wi-Fi
• Parking
• Beach Chairs
• Bicycles (4)
• Full kitchen facilities
• Brand new dishwasher
• Washer/Dryer
• Outside Patio
• Outside Pool Shower
• BBQ area
• Beach Caddy/Cart
• Beach Towels Provided
• Stand Alone Shower (Bathroom 1) Shower/Tub Combo (Bathroom 2)
• Free WiFi

***Please Note: Dog Friendly (20 lbs. and Under)
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $230
Price Per Weekfrom $1450
3 Bedroom
This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. Sea la Vie is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea la Vie offers a shared heated pool with its sister property Sea Esta (when booking Siesta Salt Life, the pool is private). The kitchen features stainless steel appliances, a dining room table that fits up to 6, and a breakfast counter. The living area features a flat screen TV and access to the outdoor private patio. With plantation shutters and coastal décor throughout, you will truly feel the charm of Siesta Key living. Each bedroom features a flat screen TV & offers unique views of the home, from the outside pool area, to the lush jungle-like landscaping of the backyard. Step outside & you’ll find a massive outdoor area featuring a tranquil pool & BBQ area: perfect for family gatherings! The outside area also features a shower station. Book Sea la Vie, and let your cares drift away. You Have Arrived…

Sea la Vie can accommodate up to 8 guests, with a bedding configuration as follows:

• Bedroom 1: King Bed (1) – Sleeps: 2
• Bedroom 2: Queen Bed (1) -Sleeps: 2
• Bedroom 3: Queen Bed (2) – Sleeps 4

Exclusive Amenities Include:

• Close proximity to Siesta Key Public Beach (access # 7 is only 207 ft. away!)
• Walking distance to Siesta Key Village shops & restaurants
• Coffee Maker
• Stainless Steel Appliances
• Plantation Shutters
• Flat screen TV
• Flat Screen TVs in each bedroom
• Complimentary Wi-Fi
• Parking
• Semi-Private Pool (when combined with both units pool is private)
• Full kitchen facilities
• Brand new dishwasher
• Washer/Dryer
• Outside Patio
• Outside Pool Shower
• Beach Chairs
• Bicycles (4)
• BBQ area
• Beach Caddy/Cart
• Beach Towels Provided
• Stand Alone Shower (Bathroom 1) Shower/Tub Combo (Bathroom 2)
• Free WiFi


***Please Note: Dog Friendly (20 lbs. and Under)
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $230
Price Per Weekfrom $1450
3 Bedroom
Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers, quartz counters and state of the art stainless steel appliances in the newly remodeled kitchen, and your very own private screened in lanai and heated pool among many other great amenities. Enjoy having four bicycles, beach chairs, a cooler and a rolling beach caddy so that your three minute walk to our pristine beach is truly effortless. No renting beach equipment necessary at Casita Morning Star! Just bring your flipflops, suntan lotion and shades!

Casita Morning Star is one of two attached Casitas that has 3 bedrooms and 3 bathrooms with its own heated private pool and private screened in lanai just a moments walk to Point of Rocks Beach. Combined with its sister property, Casita Sun Star, it is perfect for larger parties celebrating family reunions, weddings, special anniversaries, and more. There are three bedrooms, two of which feature king size beds (sleeping 2 in each room) and one bedroom that features two full beds (sleeps 4.) Enjoy a plush and comfy Queen sofa sleeper in the living room (sleeps 2). Casita Morning Star and Casita Sun Star sleeps 10 in each unit with maximum comfort because of their open and spacious floorplans.

Inside the home, enjoy an oversized washer/dryer to assure you an abundance of clean clothes and towels.

Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation of limestone rock that extends from the beach out into the Gulf of Mexico. This location has become home to a wide array of tropical fish and is not only a great environment for fishing, but the only real location for great snorkeling on the Island.

Within walking distance [most less than ¼ of a mile] you’ll find all of the great shops, markets, bars and restaurants located in the South Village-Crescent Beach area. Here you’ll find the Crescent Beach Grocery, a gourmet market that features one of the best butcher shops in Sarasota as well as an amazing wine selection. “Big Water Fish Market” located in the Crescent Beach shopping plaza at 6641 Midnight Pass Road is the only fish market available on Siesta Key. “CBs Bait and Tackle Shop” at Stickney Point Bridge offers both fishing tackle, fishing guides and boat rentals.

Restaurants in the immediate area include some of the best on Siesta Key: Miguel’s, Capt Curt’s, Turtle’s on Little Sarasota Bay, Ophelia’s on the Bay, Clayton’s Siesta Grill, Crescent Club, City Pizza and Anna’s Deli II just to mention a few. Davidson’s Drug, the US Post office and numerous souvenir shops, giftware shops, and eateries await your adventuresome spirit. Siesta Key Public beach is about 2 miles north on Midnight Pass Rd and provides parking capability for 800 cars along with restrooms, etc.

Siesta Key’s North Village is 2.8 miles north and is always a lot of fun with many restaurants, shops, and attractions. The city of Sarasota is filled with restaurants, art galleries, museums, shopping opportunities, theaters, etc., and offers much to do and see.​
Bedrooms3
Bathrooms3
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $200
Price Per Weekfrom $1375
3 Bedroom
Welcome to Casita Sun Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers, quartz counters and state of the art stainless steel appliances in the newly remodeled kitchen, and your very own private screened in lanai and heated pool among many other great amenities. Enjoy having your every four bicycles, beach chairs, a cooler and rolling beach caddy so that your three minute walk to our pristine beach is truly effortless. No renting beach equipment necessary at Casita Sun Star! Just bring your flipflops, suntan lotion and shades!

Casita Sun Star is one of two attached Casitas that has 3 bedrooms and 3 bathrooms with its own heated private pool and private screened in lanai just a moments walk to Point of Rocks Beach. Combined with its sister property, Casita Morning Star, it is perfect for larger parties ( 20 ) celebrating family reunions, weddings, special anniversaries, and more. There are three bedrooms, two of which feature king size beds (sleeping 2 in each room) and one bedroom that features two full beds (sleeps 4.) Enjoy a plush and comfy Queen sofa sleeper in the living room (sleeps 2). Casita Morning Star and Casita Sun Star sleeps 10 in each unit with maximum comfort because of their open and spacious floor plans.

Inside the home, enjoy an oversized washer/dryer to assure you an abundance of clean clothes and towels.
Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation of limestone rock that extends from the beach out into the Gulf of Mexico. This location has become home to a wide array of tropical fish and is not only a great environment for fishing, but the only real location for great snorkeling on the Island.

Within walking distance [most less than ¼ of a mile] you’ll find all of the great shops, markets, bars and restaurants located in the South Village-Crescent Beach area. Here you’ll find the Crescent Beach Grocery, a gourmet market that features one of the best butcher shops in Sarasota as well as an amazing wine selection. “Big Water Fish Market” located in the Crescent Beach shopping plaza at 6641 Midnight Pass Road is the only fish market available on Siesta Key. “CBs Bait and Tackle Shop” at Stickney Point Bridge offers both fishing tackle, fishing guides and boat rentals.

Restaurants in the immediate area include some of the best on Siesta Key: Miguel’s, Capt. Curt’s, Turtle’s on Little Sarasota Bay, Ophelia’s on the Bay, Clayton’s Siesta Grill, Crescent Club, City Pizza and Anna’s Deli II just to mention a few. Davidson’s Drug, the US Post office and numerous souvenir shops, giftware shops, and eateries await your adventuresome spirit. Siesta Key Public beach is about 2 miles north on Midnight Pass Rd and provides parking capability for 800 cars along with restrooms, etc.

Siesta Key’s North Village is 2.8 miles north and is always a lot of fun with many restaurants, shops, and attractions. The city of Sarasota is filled with restaurants, art galleries, museums, shopping opportunities, theaters, etc., and offers much to do and see.​
Bedrooms3
Bathrooms3
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $200
Price Per Weekfrom $1375
3 Bedroom
This charming 3 bedroom/3 bathroom home is located right in the heart of Siesta Key Village and just steps from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families and small groups. Reserve Mandevilla now and live like a Siesta Key local!

Mandevilla can accommodate up to 6 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: King Bed (1) - Sleeps: 2
• Bedroom # 3: King Bed (1) - Sleeps: 2

Exclusive Amenities Include:

• Heated Pool
• Close proximity to Siesta Key Beach
• Located in the heart of Siesta Key Village
• Kitchen essentials provided
• Linens Provided
• Washer & Dryer
• Outdoor lounge area
• Beach Towels
• Free WIFI



Bedrooms3
Bathrooms3
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $150
Price Per Weekfrom $1000
3 Bedroom
This inviting 3 bedroom/3 bathroom home is located right in the heart of Siesta Key Village and just steps from Siesta Key Beach, voted the # 1 beach in the USA! Reserve Honeysuckle now and live like a Siesta Key local!


Honeysuckle can accommodate up to 10 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: King Bed (1) - Sleeps: 2
• Bedroom # 3: King Bed (1) - Sleeps: 2
• Living Room # 1: Sleeper Sofa (1) - Sleeps: 2
• Living Room # 2: Sleeper Sofa (1) - Sleeps: 2

Exclusive Amenities Include:

• Heated Pool
• Close proximity to Siesta Key Beach
• Located in the heart of Siesta Key Village
• Kitchen essentials provided
• Linens Provided
• Washer & Dryer
• Secure parking in lot
• Screened-in lanai
• Beach Towels
• Dog-friendly (up to 25 lbs.)
• Free WIFI



Bedrooms3
Bathrooms3
Rental TypeHouse
Pet Friendly?
Price Per Nightfrom $150
Price Per Weekfrom $1000
3 Bedroom
This exquisite 3BR/2BA cottage is centrally located close to the Village and Siesta Key Beach, continually ranked as one of the top ten beaches in the USA! This home is ideal for small groups and families.

La Contento Casa can accommodate up to 8 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) – Sleeps: 2
• Bedroom # 2: King Bed (1) – Sleeps: 2
• Bedroom # 3: Twin Bed (2) – Sleeps: 2
• Extra Beds: Rollaway Bed (2) – Sleeps: 2


Exclusive Amenities Include:

• Private Heated Pool
• Kitchen Essentials Provided
• Linens Provided
• Water Views
• Brand-New Kitchen
• Stainless Steel Appliances
• Indoor Dining & Lounge Area
• Boat Dock
• Kayaks (2)
• Paddleboard (1)
• Beach Caddy
• Beach Cooler
• Bicycles (4)
• Screened-In Lanai
• Beach Chairs
• Beach Towels
• Grill
• HDTVs in Living Room + Each Bedroom
• Free WiFi


Please Note: There is a 1 rental per 30-day period, per Sarasota, FL ordinance, contact us for more information.

Please note that your reservation must follow under the accordance of the Sarasota County code regulations.
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Weekfrom $2695
3 Bedroom
Welcome to the completely remodeled, and newly furnished Sand Dollar Cottage!

This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy the peacefulness of a large heated pool with beautiful and breathtaking views of the water via the Intracoastal canals of Siesta Key island. The home features a brand new professional kitchen, with new stainless steel appliances, and a bar counter that connects the kitchen to the living room, perfect for cooking large family meals or entertaining all of your friends and family. Just off of the kitchen is a formal dining room that seats 8 comfortably, which makes gatherings for family meals a breeze. The kitchen also features a sliding glass door that instantly connects the indoor kitchen to the outdoor pool area, and enough lounging to seat 8 and more, whether you prefer to lounge poolside, or relax in the screened in lanai. The chef of the evening will easily be able to entertain and converse with anyone and everyone whether they are lounging in the pool area or relaxing in the living room, all at the same time.

The living area features absolutely breathtaking views of the Grand Canal, with sliding glass doors that pocket back and open to the screened in lanai by the heated pool. There is no better feeling than to bring the outdoors in, by opening the sliders in cooler weather and letting the sounds of nature soothe the soul. This also makes for twice the amount of space for gatherings and parties with the living room directly connected to the screened-in lanai where you will find another table for dining as well as a lounging area.

Each bedroom features a new HDTV with premium cable channels. Enjoy the plush luxurious comforts of top quality bedding and linens, and brand new furniture and mattresses in each room. The bedspreads are bold and vivacious, the pillows are plush, and the linens are so soft, rest will come naturally and immediately, especially with the comfort of specialized pressure relief mattresses designed to relieve any aching body.

The bathroom cabinetry and wall units provide plenty of space for personal belongings, but enjoy the comforts of plush white bath towels, hair dryers and vanity mirrors in each bathroom.

Outdoors, the world of Siesta Key awaits you and your family and friends.... and this home boasts numerous ways to explore the exciting life of "island living!" Take the beach bicycles (4) for a spin and get to know our little island, safely and comfortably. The island is just the right size to explore entirely, and with gentle peddling you'll find everything is within minutes of the Sand Dollar Cottage. Once you have explored our island by land, try by sea.... the home features two kayaks, which is the perfect way to venture out and see all the interior canals of Siesta Key. Beautiful neighboring homes, gorgeous landscaping, and plenty of exquisite wildlife sightings will certainly fascinate you by kayak!

After all the adventure, a night of relaxation and rest is awaiting you. Crank up the new gas grill by the pool and cook a BBQ for the family while taking a dip in the refreshing pool (heated for your winter stays) and just sit back and watch the night sky turn dark, as the stars begin to shine down reminding you of just how perfect your day has been....

Release your worries, your tension, your everyday life and embrace the warmth from the sun, the salt in the air, and the cool breeze off the gulf. Embrace your vacation. We are here to make your stay feel like a dream come true. Your moments with us are cherished and we appreciate the reasons you chose us, and we can prove it. Welcome, friends!

*Sarasota County ordinance limits rentals to 12 per year, so 2 week or longer rentals may be required in certain months. Minimum stay requirements are not listed here. One week rentals MAY be considered with an additional charge applied. Please inquire with one of our Vacation Specialists to discuss availability and rates. We maintain our calendars using an internal reservation system.

Please note that your reservation must follow under the accordance of the Sarasota County code regulations.
Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Weekfrom $2695
3 Bedroom
This luxurious and recently renovated (as of 2019) 3-bedroom/2-bathroom home is located in close proximity to Siesta Key Village and just minutes to Siesta Key Beach, voted the #1 beach in the USA! Immaculately decorated and with your every comfort in mind, you will truly be living a life of luxury right here on Siesta Key! This home This home is perfect for families and small groups.

Ventana Rosa can accommodate up to 10 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: King Bed (1) - Sleeps: 2
• Bedroom # 3: Queen Bed (1) - Sleeps: 2 + Twin Bed (2) - Sleeps: 2
• Living Room: Sleeper Sofa (1) - Sleeps: 2


Exclusive Amenities Include:

• Private Heated Pool
• Outdoor covered porch area (400 square feet of living space!)
• Stainless Steel Kitchen Appliances
• Linens Provided
• Beach Caddy
• Beach Chairs
• Beach Towels
• Outdoor Dining/Lounge Area
• Dishwasher
• Washer/Dryer
• Secure Parking
• Outdoor Bathroom with Shower
• Outdoor cornhole Set
• Wall-Mounted Flat Screen TVs throughout Home + 1 Outside
• Dog-Friendly (Up to 25 lbs.)
• Free Wifi




Bedrooms3
Bathrooms2
Rental TypeHouse
Pet Friendly?
Price Per Weekfrom $975
3 Bedroom
This quaint 3-bedroom/2.5-bathroom home is located near Siesta Key Village and just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for small families and couples alike.

Coral Breeze can accommodate up to 8 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: Twin Bed (2) - Sleeps: 2
• Bedroom # 3: Queen Bed (1) - Sleeps: 2
• Living Room: Sleeper Sofa (1) - Sleeps: 2


Exclusive Amenities Include:

• Private Heated Pool
• Stainless Steel Kitchen Appliances
• Secure Parking in Garage
• Kitchen Essentials
• Breakfast Counter
• Linens Provided
• Outdoor Lounge Area
• Beach Caddy
• Cooler
• Beach Towels
• Regular Coffee Maker
• Dishwasher
• Free WIFI



Bedrooms3
Bathrooms2.5
Rental TypeHouse
Pet Friendly?
Price Per Weekfrom $2600
3 Bedroom
This captivating 3-bedroom/3-bathroom townhome features all the amenities you can think of for your beach vacation and offers an unbeatable location. With beach decor throughout, you will truly be living the "Beach Life." Villa Castile is centrally located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families and small groups.

Villa Castile can accommodate up to 10 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2
• Bedroom # 2: King Bed (1) - Sleeps: 2
• Bedroom # 3: Queen Bed (2) - Sleeps: 4
• Living Room: Sleeper Sofa (1) - Sleeps: 2

Exclusive Amenities Include:

• Hot Tub
• Bar Area
• Gas Grill
• Outdoor Seating Area
• Washer/Dryer
• Dining (Seats up to 8)
• Bikes (4)
• Secure Parking in Garage
• Gourmet Kitchen
• Beach Caddy
• Beach Chairs
• Cooler
• Free WIFI
• Dog-Friendly (Up to 30 lbs.)
Bedrooms3
Bathrooms3
Rental TypeTownhome
Pet Friendly?
Price Per Nightfrom $175
Price Per Weekfrom $1700
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