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La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Photo gallery for La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Whether you're floating under blue skies or cooling off after the beach, this pool is pure island bliss.
Aerial view showing La Contento Casa's ideal location—just a short walk to Siesta Key Beach powdery white sands.
Evenings are magical here—take a dip under the stars and feel the day melt away.
Start your mornings with a peaceful swim.
This poolside lanai invites you to slow down and unwind.

Reviews

9.8 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Discover nearby landmarks
    Near Siesta Key Beach
3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Private pool
  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪9 min walk‬
  • Place, Siesta Key Beach Playground
    ‪9 min walk‬
  • Place, St. Boniface Episcopal Church Labyrinth
    ‪9 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds

Common Space

2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

About this property

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

"🌴 La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beach

💖 Why You'll Love This Home
Awaken to sun-drenched mornings and tranquil canal views in this inviting waterfront retreat. La Contento Casa offers a seamless blend of indoor comfort and outdoor serenity, promising an escape where every moment feels like a breath of fresh air.

👨‍👩‍👧 Perfect For
Families seeking a memorable beach vacation, couples desiring a peaceful waterfront escape, or small groups looking for a comfortable and convenient base to explore Siesta Key.

🎞️ Imagine This
Your day begins with a gentle breeze drifting in as you relax on your covered back porch, watching the palms sway. After a leisurely breakfast prepared in the gourmet-grade kitchen with its convenient window pass-through to the patio, you gather your beach essentials—provided for your convenience—and take the short, invigorating 10-minute walk to Siesta Key Beach, feeling the world-famous white sands beneath your toes.

Back at La Contento Casa, the private heated pool is waiting, followed by an afternoon lounging by the water, perhaps with a drink crafted at your outdoor bar with sink. As evening approaches, the scent of a home-cooked meal fills the air, enjoyed alfresco with the canal views as your backdrop. Later, unwind in the spacious living area, sharing stories and laughter, before drifting off to sleep in one of the comfortable king beds, dreaming of another perfect day in paradise.

🛌 Where You'll Sleep
- Bedroom 1: King Bed, shared bath, main floor, TV
- Bedroom 2: King Bed, shared bath, main floor, TV
- Bedroom 3: Two Twin Beds, shared bath, main floor, TV
- Bonus Room: Two Rollaway Beds, located in common area

📍 Explore the Area
Discover the best of Siesta Key with ease. 0.4 miles to Siesta Key Beach, renowned for its crystal-white quartz sand. Enjoy a delightful stroll or quick drive to Siesta Key Village (1.4 miles), offering an array of charming boutiques, diverse dining options, and vibrant coastal energy.

📝 Your Siesta Key Escape Awaits
Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.

Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This pool is heated between November 15 - April 15. Please note: There is 1 rental per 30 day period, per Sarasota, FL ordinance. Contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations."

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4266796
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Siesta Key

Located in Siesta Key, this holiday home is in the city centre and on the waterfront. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Looking to enjoy an event or a game while in town? See what's going on at Ed Smith Stadium, or consider a night out at Robarts Sports ARENA. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 9 min walk - 0.8 km
  • Siesta Key Beach Playground - 9 min walk - 0.8 km
  • St. Boniface Episcopal Church Labyrinth - 9 min walk - 0.8 km
  • Siesta Key Farmers Market - 2 min drive - 2.1 km
  • Crescent Beach - 6 min drive - 3.8 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 34 min drive

Restaurants

  • ‪Siesta Beach Pavilion - ‬12 min walk
  • ‪Circle K - ‬5 min drive
  • ‪Siesta Key Snack Bar - ‬12 min walk
  • ‪Gilligan's Island Bar & Grill - ‬4 min drive
  • ‪Sun Garden Cafe - ‬4 min drive

Frequently asked questions

Is La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!?

As of 20 June 2026, prices found for a 1-night stay for 2 adults at La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks! on 24 July 2026 start from AU$2,878, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!?

On-site parking is available at the property.

What time is check-in at La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!?

Check-in begins at 4:00 PM.

What time is check-out at La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!?

Checkout is at 10:00 AM.

Where is La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks! located?

Located in the heart of Siesta Key, this holiday home is within a 15-minute walk of St. Boniface Episcopal Church Labyrinth and Siesta Key Beach. Crescent Beach is 2.2 mi (3.5 km) away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 9 out of 11 reviews
Rating 8 - Good. 2 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

9.6/10

Cleanliness

10/10

Check-in

9.2/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Mary W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was beautiful! It was our favorite rental.
Stayed 14 nights in Jan 2026
Response from VrboOwner on 17 Feb 2026
Hi Mary, Thank you so much for your kind words! We’re thrilled to hear that our home was your favorite rental and that you enjoyed your stay. We’d love to welcome you back anytime! Regards, The CottageCrew
Verified

10/10 Excellent

Trisha R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay at La Contento

Perfect house, great location, amazing outdoor space. Everything we needed.
Stayed 7 nights in Dec 2023
Response from VrboOwner on 19 Jan 2024
Dear Trisha, Thank you for your wonderful review! We're thrilled to hear that La Contento Casa was a perfect fit for your stay, offering a great location and amazing outdoor space. Providing everything you needed is exactly what we aim for. We appreciate your kind words and hope to welcome you back to Siesta Key Village soon! Best regards, The CottageCrew
Verified

10/10 Excellent

Kate D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So content with Casa Contento

The property was exactly as advertised. The heated pool was amazing. The decor was beautiful and was in close proximity to town and the beach. We loved our stay and would definitely stay again!!
Stayed 8 nights in Apr 2021
Response from VrboOwner on 2 July 2023
Hi Kate, Thanks so much for this lovely review of La Contento Casa! We are so happy to hear that you enjoyed the pool and location. We hope to host your next stay in beautiful Siesta Key! With Love, The CottageCrew
Verified

10/10 Excellent

Jackie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful House

We had a wonderful vacation in SK and this home base was the best thing about it. The house is on a very quiet street but really close to anywhere you could possibly want to go. Upon arrival, house was super clean - which I'm quite picky about. The beds were all very comfortable. The pool was a dream. The house is the best stocked vrbo we've ever stayed in. It has everything you could ever need. Property managers were super responsive - had a slow sink drain and someone was there in a flash to snake it. Really had a great time and can't recommend this house enough!
Stayed 14 nights in Jul 2022
Response from VrboOwner on 2 July 2023
Hi Jackie, Thank you for sharing such a kind review! We are absolutely thrilled to hear about your wonderful vacation experience at La Contento Casa. We are so appreciative and will pass on the compliments to the rest of the crew. The pool is magnificent, as well as the views of the intracoastal! We hope to see you again soon for another fantastic vacation. (: With love, The Cottage Crew
Verified

10/10 Excellent

Shawna E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great updated home and great location

The house we great and very nicely updated. The outdoor area was fantastic. My only very minor complaint is that other than typical kitchen supplies, dishes, etc, there was absolutely nothing in the kitchen in terms of condiments, etc. Not even a shaker of salt or coffee filter. Not a huge deal, but many other places we have stayed have had at least some basic supplies. But otherwise, really great place.
Stayed 14 nights in Jul 2022
Response from VrboOwner on 2 July 2023
Hi Shawna, Thank you so much for sharing your experience with us! We are so happy to hear you loved the home, the location is definitely a highlight. We appreciate the honest feedback and hope to host your stay again soon! (: With love, The Cottage Crew
Verified

10/10 Excellent

Heidi J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for families!

Our family of seven, plus our little dog, stayed here for a week over Christmas and really enjoyed it. We brought bikes and were able to get to the beach or shops in a few minutes. The home is in a quiet cul-de-sac. Free public tennis courts near the beach were generally available. You had to bring your own nets for pickle ball— seemed like most open pickle ball play was in Sarasota. The heated pool was tolerable when the outside temperature was at least 65. Great towels, comfortable beds, great closet space. We really enjoyed the music at the Catholic Church close by. A few notes— it was very challenging to enter our kayaks out back when we were there, due to the low water level. Bring a rope. And then, we have stayed in many Vrbos over the years, and I did not come prepared to find this one had no bath soaps at all. Also, not even starter coffee, and no salt/pepper. I appreciate places that have basics—especially at this price! And they made a careful note about being honest about the number of your guests, and when we seven arrived, there were exactly THREE welcome cupcakes 😂 Anyway, overall I highly recommend this home, just come prepared as above!
Stayed 8 nights in Dec 2022
Response from VrboOwner on 2 July 2023
Hi Heidi, Thank you so much for sharing such a kind 5 star review! We are so thrilled to hear you enjoyed your stay at La Contento Casa and were able to take advantage of all the amenities available, especially the canal access. However, we do appreciate your honest feedback and can work on potentially adding these minor yet important details to you and our future guests! We thank you for bringing all of this to our attention and are glad you were still able to relax on your family getaway. Should you find yourself wanting another vacation in paradise, we would love to host your stay again! (: With love, The Cottage Crew
Verified

8/10 Good

Patrick B.

Liked: Check-in, location, listing accuracy

Contento

Fabulous neighborhood on the Key. Owners did a lot of renovations and upgrades to the home after the purchase. However, cleaning crew needs to do a better job of cleaning prior to arrival. Also, it appears the electrical service may need some upgrades and there was some presence of mold in the garage cabinets that will need to be inspected. However, the overall stay was great for a family of 4. Finally, the pool was fabulous since red tide was a concern.
Stayed 17 nights in Jul 2021
Response from VrboOwner on 2 July 2023
Thank you so much for your review. You are our eyes on the property and we will reach out to you shorty requesting additional information so that we can fix these issues. -The CottageCrew
Verified

10/10 Excellent

Denise T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved this house.

+++ loved the house, towels, beach equipment, bay to fish, kayaks, paddle boards, lights, smelled clean, cupcakes and thanksgiving pie 🥧 - is there a dog or a cat? Lots of fur on the pillows and blankets. Something that was not ours in the closet on a blanket. (Maybe someone was sick and it was not washed) Perfect otherwise!! Thank you 4.9 rating
Stayed 8 nights in Nov 2020
Response from VrboOwner on 2 July 2023
Hi Denise, We are so glad to hear that you enjoyed your stay at La Contento Casa! Thank you providing this helpful feedback, our Guest Services department will be notified. We hope to host your next stay in beautiful Siesta Key! With Love, The CottageCrew
Verified

10/10 Excellent

Ian W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at excellent property

Excellent property - would be happy to stay there again
Stayed 8 nights in Aug 2019
Response from VrboOwner on 2 July 2023
Ian, Thank you so much for your review of La Contento Casa! We can't wait to host your stay again the next time you are in beautiful Siesta Key. Until next time, #CottageOn! With Love, The CottageCrew
Verified

10/10 Excellent

Martin C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

If not for the weather

Everything exactly as advertised, which made heavy rain days bearable because of the outdoors living area under their roof. Sunsets are amazing !
Stayed 14 nights in Jun 2019
Response from VrboOwner on 2 July 2023
Martin, Thank you for your review of La Contento Casa! We are thrilled you enjoyed your stay with us. We completely agree with you, Siesta Key sunsets are the best sunsets! We can't wait to host your stay again the next time you are in beautiful Siesta Key! Until next time, #CottageON! With Love, The CottageCrew
Verified

8/10 Good

James L.

Stayed 14 nights in Feb 2026
Response from VrboOwner on 8 Apr 2026
Hi James, Thank you so much for taking the time to leave a review, we're so glad to hear you enjoyed your stay at La Contento Casa. We always aim to provide a 5-star experience for our guests, so if there’s anything you feel we could improve or enhance for the future, we’d truly appreciate any feedback you’re open to sharing. We hope to welcome you back to The Cottages on the Key for another memorable stay soon! Warmly, Guest Services Team

About the host

Hosted by The Cottages on the Key, Inc.

Host profile image

What makes this property unique

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!

Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests
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