La Contento Casa – 5560

La Contento Casa - 5560
3 Bedrooms 2 Bathrooms House in Siesta Key
from $2695 per /wk
from $8085 per /mo

Property Details

Property Description

Welcome to La Contento Casa, one of Siesta Key’s most alluring 3BR/2BA canal-front cottages, with private heated pool and breathtaking views of Siesta Key’s intracoastal waterway!

Property Details

This home could qualify for our BookCareFree promotion for 2021 arrivals
This includes:
• Lenient Cancellation Policies
• Deferred Payments
• Adjusted Deposit Amounts
Ask us about how you can qualify for this special offer!

We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened our cleaning crews by mandating the highest quality products that are EPA approved to use against COVID-19. Our cleaners also have a longer period of time to complete this thorough process to ensure a full cleaning of all items. After this initial cleaning, we require the cleaning company manager to assess the job completed and assign any additional areas to be cleaned. Furthermore, right before your arrival, we have a quality control team that conducts a 50-point pre arrival inspection on this home and reapplies the approved products once again right before your walk into your beautiful home. We extensively re-clean every light switch, lamp, door knob, surface, remote, hard back chair, and any area that is considered a high volume touch surface with approved disinfectant cleaning material. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our cleaning services have enhanced protocols in place to ensure that you feel tremendously safe and happy with this amazing home. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!

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)
• Beach Caddy
• Beach Cooler
• Bicycles (4)
• Screened-In Lanai
• Beach Chairs
• Beach Towels
• Grill
• HDTVs in Living Room + Each Bedroom
• Free WiFi
• Dog-Friendly with a Fee (1 dog up to 25 lbs.)

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.

This property has
  • Bedroom #1: King Bed (1)
  • Bedroom #2: King Bed (1)
  • Bedroom #3: Single Bed (2)
Booking Calendar

Availability & Booking Calendar


Property Location



  • Concierge - Other Services
  • Bay
  • Coin Laundry
  • Health Beauty Spa
  • Marina
  • Museums
  • Parks
  • Water Parks
  • Winery Tours
  • Zoo
  • Satellite / Cable
  • Television
  • Air Conditioning
  • Central Heat
  • Clothes Dryer
  • Garage
  • Hair Dryer
  • Heating
  • Internet - Hi Speed
  • Internet - Wireless
  • Iron and Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Cookware
  • Dining Area
  • Dining Spices
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Antiquing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Gambling
  • Outlet Shopping
  • Paddle Boat
  • Shopping
  • Water Sports
  • Wildlife Viewing
  • Hospital
  • Laundromat
  • Beach
  • Near Ocean
  • Village
  • Water View
  • Waterfront
  • Balcony
  • Bicycle
  • Deck/Patio
  • Gas Grill
  • Heated Pool
  • Private Pool
  • Basketball Court
  • Biking
  • Deep Sea Fishing
  • Fishing
  • Fishing Bay
  • Fishing Fly
  • Fishing Surf
  • Golf Optional
  • Golfing
  • Hiking
  • Jet Skiing
  • Kayaking
  • Paragliding
  • Parasailing
  • Pier Fishing
  • Roller Blading
  • Sailing
  • Scuba or Snorkeling
  • Snorkeling
  • Surfing
  • Swimming
  • Water Skiing
  • Water Tubing
  • Wind Surfing
  • Family
  • Luxury
Rates & Policies


Weekly Rate: $2695 - $7000 per week
Monthly Rate: $8085 - $15750 per month
- Rate varies due to seasonality and holidays.
- Please select your dates on our online booking calendar for an exact quote.


Accomodations Tax - 12.00%
Lost and Found Fees - $0.00 - Tax Exempt
Administrative fee - 9.00%
Accidental Damage Protection $3000 Coverage - $75.00
Pet Fee - $250.00
Exit Cleaning Fee - $225.00
Cancellation Policy
CANCELLATION POLICY / TRIP INSURANCE NOTICE: Regarding this reservation process, The Cottages on the Key Company is creating a legal, binding contract between the property owner and the guests to insure the desired benefits to each of the parties. The Cancellation Policy for prime season rentals [December – April, June-August] stipulates that any rental deposit amount and any additional payments made are refundable less any administrative fees up to ninety [90] days prior to the beginning of the rental period. After 90 days prior to the rental period, the Licensor shall have the uncontested right to retain the initial Deposit and any other payments received. If you cancel and your check-in date is more than ninety [90] days away, you will receive a refund of your deposit less the administrative fee by credit card refund within 15 days of your written cancellation notice. The Cancellation Policy for all other reservations in the periods of September – November, and May stipulates that any rental deposit amount and any payments are refundable less any administrative fees up to seven [7] days prior to the beginning of the rental period. After 7 days prior to the rental period, the Licensor shall have the uncontested right to retain the initial Deposit and any other payments received. The Cottages on the Key company strongly recommends purchasing a TRIP INSURANCE POLICY to insure recovery of your deposit/payments made and potentially retained by this Cancellation Policy to avoid loss during unforeseen circumstances. We recommend researching trip insurance companies online. We also offer an option of purchasing trip insurance at the time of your booking with The Cottages on the Key upon request. Guests may also purchase the trip insurance up to 24 hours prior to their arrival. Please note: there is an option for cancelling for any reason (CFAR) up to 20 days within the initial deposit date. We would recommend you research this type of policy from various providers to include iTravelInsured:

Please note: if you booked using a 3rd party affiliate (i.e. HomeAway or VRBO), please refer to their cancellation policy for your records.
Last updated 01/22/2021
Deposit Policy
Please sign online with digital signature. This agreement must be returned to us within 48 hours, as we cannot guarantee your requested dates without receipt of a signed rental agreement. In order to finalize your reservation, we require the initial deposit plus a credit card on file to cover any incidentals and negligent damages.
Last updated 01/22/2021

Guest Reviews

Great stay at excellent property by Ian W. 08/12/2019
Excellent property - would be happy to stay there again
If not for the weather by Martin C. 07/16/2019
Everything exactly as advertised, which made heavy rain days bearable because of the outdoors living area under their roof. Sunsets are amazing !
The house and property are magnificent by Igor and Dubravka T. 07/23/2018
We spent the last 2 weeks at La Contento on Siesta Key. What a beautiful place!

The house and property are magnificent - the house is beautifully decorated, cozy, and clean. It has every amenity possible, including beach towels, beach chairs, and a cupboard with the basic necessities. The pool area and the lanai is where we spent most of our time, and truly enjoyed them. From sunset to sundown, the property brought us joy and happiness! After an overnight storm, your pool staff came by quietly and cleaned the pool and pool area before we woke up - that is superb customer service!

Thank you also for your professionalism and quick response times. You were able to help me with every question and request I had during the booking process, and during our stay.

Thank you, and we look forward to staying with you again in the near future!

I am a bit delayed in writing this review.... by Sarah C. 08/28/2017
I am a bit delayed in writing this review.... about a year delayed. Better late than never 🙂 I had such a pleasant experience with Cottages on the Key. From the booking to the actual home and everything in between. We stayed at the La Contento property for a couple weeks in Sept 2017. The moment we arrived at the home we were very happy. It had everything it listed and more. To add, we had some delicious cupcakes waiting for us. Everything was very clean and beautifully decorated. The pool very welcoming. Being right on the canal, the Cottages recommended a boat rental service that brought the boat right to the house and we had the boat for 5 days. Fabulous. It was our home away from home...we can't wait to return.
An amazing location for wildlife watching, the garden, the canal and out on the water. by sarah m 08/23/2017
This is our second visit to Cassa Contento within two years. We just love it so much. The beautiful waterside house is situated on the canal, it is close to the beach, there are kayaks and bikes to use, and its just a short cycle ride into the village - what more could you ask for! The beds are super comfy, the bedrooms and bathrooms are spacious and the furniture and decor is beautiful. This house is kitted out with every thing you need to make it your home.
Incredible home with everything you want!! by Eldodgemous 07/12/2017
We had an incredible stay at Casa Contento. This place is in a perfect location on the canal and only a short walk/cycle to the beach and village. The pool is amazing and great size to smash out some lengths. The house has everything you could imagine you may need from bikes, BBQ, kayaks to all beach accessories. It's immaculate and the decor has been done with such care and attention. If you get bored of the amazing outdoor space, the TV has an infinite amount of channels so you can just relax in the cool AC. From the minute you step in, you are on holiday. Will definitely be back soon...
Waterfront, stylish luxury with an enormous pool by Clare 03/09/2017
If you're looking for a remodelled and newly furnished spectacular canal front property with stylish decor and a breathtaking pool - look no further. Casa Contento is within walking distance of both the beach and the village for nightlife and dining and comes complete with Bicycles, Kayaks and even a paddle board for the more adventurous. We stayed for a fortnight in September and loved using the kayaks on the canal where we saw Manatees, the bikes were used every evening to cycle into the village for dinner and cocktails and the gardens at the property are just beautiful. The property has a fantastic lanai which includes an outdoor kitchen area and grill so we tended to cook out regularly too. We fell in love with this little slice of heaven so much that we immediately booked to stay again in May and August 2017!!