FEATURED COTTAGES

SOME OF THE BEST COTTAGES AVAILABLE

There are so many choices when deciding where to travel and even more options on where to stay. All of our cottages have access to heated pools, gas grills, bikes and so much more. Here are a few of our contenders for your review. While many say they provide the best places, our CottageCrew takes time to curate, update and change properties based on traveler input from people just like you (yes that does include getting larger blenders in some locations) …we the indulgers!

A Siesta Key waterfront cottage near beach features 2 bedrooms & 2 bathrooms. Enjoy heated pool, spa, sundeck, lush landscaping & private canal dock. Book with Villa Champagne to become Sophies Quartier - great for groups!

DETAILS

A combo of the Casa Tegula and Casa Stolida homes, is walking distance to the beach. Each cottage has 4 bedrooms, 3 bathrooms, their own heated pool and private cabanas.

DETAILS

A 2 bedroom/1 bathroom Siesta Key vacation home with a shared heated pool. When reserved with Casita Coco to become CocoBayou Cottage, you can sleep up to 10! Near beach, Crescent Village & the Intercoastal.

DETAILS

207 FT from beach access this cottage (part of Siesta Salt Life) provides exceptional amenities and one of the best locations on the key!

DETAILS

Featuring two bedrooms, sleeping den, 2 full bathrooms, a gourmet kitchen and a shared heated pool with a waterfall feature! Near beach access & sleeps up to 6!

DETAILS

TRAVEL YOUR WAY

SELECT YOUR TRAVEL DATES | SELECT AN ADDED BENEFIT

STAY TWO WEEKS - AND CHOOSE AN ADDED BENEFIT THAT WORKS BEST FOR YOU AND YOUR FELLOW TRAVELERS*...

COTTAGE LOCATION

SELECT YOUR DESIRED COTTAGE LOCATION

One Sun > One Beach > One Key with so many properties to choose from! No matter where you stay on the key, it takes moments to get from one end to the other even without a vehicle! With a local free trolley and free-ride^ car services for the last minute adventurers and safe fun-seekers, Siesta Key’s transportation options have opened a whole new way to experience our island! As with any destination, it’s great to have the input from those that live and experience the surrounding area, so don’t hesitate to give us a call and we can help accommodate your needs and desires when narrowing down cottage options!

PACKAGES

EXCLUSIVE COTTAGES

People First

Our mission is not just to provide the best possible properties… doing so is a natural evolution of our primary drive, which is to provide you the best possible memories. We pride ourselves on our interactions, our understanding, and growing global network of friends. If you choose to stay elsewhere and need some local information, we are still here for you. Because …we the travelers (includes our adventures as well)!

Schedule A Call

There are no additional fees for booking over the phone or on-line, we will walk through your available options when you have time! Simply select a desired date below, then any available time and provide the required information. Within the next few hours, you will receive a notification that the request is confirmed and we will call you on that date and time with vacation home options that fit your criteria! #CottageON

https://thecottagesonthekey.com/
December 2018
Mon Tue Wed Thu Fri Sat Sun
262728293012
3456789
10111213141516
17181920212223
24252627282930
31123456

Crescent Cottage

An absolute one of kind, limited edition home that exudes beauty, profoundness, and intelligence featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock.

$ 310

Crescent Cottage

An absolute one of kind, limited edition home that exudes beauty, profoundness, and intelligence featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock.

Honey Mango Cabana

This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Honey Mango Cabana can be reserved alone or along with Juicy Mango Cabana for big families or groups.

$ 152

Honey Mango Cabana

This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Honey Mango Cabana can be reserved alone or along with Juicy Mango Cabana for big families or groups.

The Conch

A luxury vacation home is comprised of two units, Casa Coquina & Casa Antilles. Ideal for large groups - up to 26.

$ 712

The Conch

A luxury vacation home is comprised of two units, Casa Coquina & Casa Antilles. Ideal for large groups - up to 26.

Topsail Cottage

A luxury 3-story Siesta Key vacation home with an elevator & near beach is ideal for groups up to 12. Enjoy amazing views, heated pool & patios with kitchen, a living area, 1 bathroom and 1 bedroom on 1st floor.

$ 380

Topsail Cottage

A luxury 3-story Siesta Key vacation home with an elevator & near beach is ideal for groups up to 12. Enjoy amazing views, heated pool & patios with kitchen, a living area, 1 bathroom and 1 bedroom on 1st floor.