
Villa vacation rentals in Siesta Key
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Top-rated villa rentals in Siesta Key
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Popular amenities for Siesta Key villa rentals
Villa rentals with a pool

The Sea House
Couldn’t have found a better place to stay for our trip. After full days at the beaches, sightseeing, and exploring it was so nice to get back to our little house to enjoy the quiet and relaxing oasis. Truly a wonderful place to stay.

Luxurious Poolside Retreat in Sarasota
Alex was very professional and promptly addressed any issues we had. By issues I mean, getting us more towels and fixing the pool where it was losing water. Would definitely recommend this place!

SEALAND 3/2 Modern Villa w/ Pool near Siesta
This was one of the BEST air b&b’s I have stayed at in Sarasota so far!! Aside from the beautiful weather Inas home was very clean, and had all the amenities needed!! The pictures look exactly like what her home has to offer. She was very responsive and kind. We asked for the pool heated for the extra daily charge and she did it immediately! Very close and convenient to all grocery stores, gas stations and restaurants. About a 10 minute ride to beautiful siesta key beach. I give 10 Stars !!! Highly recommend!! Thank you Ina for hosting us and we hope to be back soon !!!! For the next guests enjoy!!

Charming 2/2 Village des Pins close to Siesta Key
This villa was very quiet and private. The view of the surrounding area from the lanai was especially enjoyable. It is just a short walk to the pool and to the outdoor grills. The circle is a great place to get a walk in anytime, day or night. The neighborhood is quiet and has a very safe and friendly feel. Clara went out of her way to help when called upon.

Dolphin Cove Waterfront St. Pete Beach w/ Pool
Beautiful home with a great water view with lots of wild life to observe. Easy to get food delivered and off street parking. We loved this place!

Starfish House - 2bed/2bad
This place is so cute! We had a great time - the pool is literally right off the unit. It is heated so if you are coming during the winter or late fall/early spring months then you can swim in the pool. The house is also next to the beach, and literally next to the beach so you can comfortably walk over. Everything was clean and this is a very stocked unit. We loved the air fryer.

Happy Place, full refund*, poolheat, sleeps 6
We enjoyed our peaceful stay. It was great for our 9 week old grandson. We loved the pool. Hopefully if we come back again more beaches will be open.

Luxury waterfront in the heart of treasure island
Jeff was exceptional. Very friendly and responsive. His home was gorgeous- just as the photos depicted. Beautiful fireplace in the living room (to take the chill off this year’s cold snap) and one in each bedroom. Such a nice touch. The unit and building met our needs perfectly. Great for two couples or a family that wants gathering space and also privacy. The condo was stocked with all the basic things you’d need! We’d highly recommend Jeff and this condo.
Villa rentals with a hot tub

Peaceful bright home minutes from the beach
Great Home. The pool made my stay, it felt like an oasis in the Florida heat.

King 1 Br/1Ba, Hot Tub - Close to Beach & Downtown
The house was a little smaller than expected, but still had everything we were looking for. We had a slight problem with the lights in the bathroom during our second day, but Eric was quick to respond to our concerns and helped us resolve the issue. The hot tub was an amazing added feature which we utilized every night and the instructions for check-in and check-out were clear and concise and easy to understand. Overall we had an amazing experience and I would highly recommend any couple to stay in this Airbnb.

Waterfront Condo w/ Kayaks, Resort Pool, Sarasota
Wonderful vacation! The unit is located on an inlet in Sarasota on the second floor. About a mile or two from downtown Sarasota, 11 minutes from Lido beach and 22 minutes from Siesta Key beach. We enjoyed both beaches but preferred the proximity and low key vibe of Lido beach. Publix and Walmart a mile or less from the unit. Very close proximity to lots of great restaurants and St. Armand’s circle for shopping. The unit was perfect for our family and there are two sleeper sofas in addition to the queen bed located in the master. The saltwater pool is just a short walk. There are two gas grills in the pool area open to the public that we used to grill steaks a night. The kitchen is stocked with everything that you need for cooking. We would book this unit again. The host was responsive and provided all information needed for our stay.

Family Oasis-Beautiful House-Infinity Pool-Beaches
We loved staying here with our family for spring break. Very family friendly and enough space for the 10 of us who went. Martin was extremely responsive. We would absolutely stay here again!

Near Siesta Key, Private, Steps to pool!
The location was great for work, the place had all the amenities that were needed during my stay.

Beautifull 2 bedroom villa, close to Siesta Key
Comfortable, cozy, clean and convenient. Appreciated all the supplies for a two week stay. I have stayed at other location that have provided an extra roll of tp and 2 detergent pods. Would definitely stay at Sue’s place next time if available. Thanks Again John

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key
Agata's villa was perfect and she was very responsive when we had a question. We appreciated the well equipped kitchen, modern appliances, lanai dining table, the reading lights and comfortable furniture in the living room, the bathtub as well as shower in both bathrooms, the Smart TV (there are three TVs), and the beach and children's equipment in the garage. The complex is lovely, peaceful and private -- a good place to take a walk, swim in the pool, play pickleball with an active group, use the billiards table in the clubhouse, join in on occasional activities such as bingo or trivia. The area is close to grocery shopping, The Legacy Trail for biking, Tamiami Trail and convenient for traveling to area beaches. We plan to go back here again and again. Thank you, Agata!
Private villa rentals

Booking for Summer! Short walk to the beach-Unit A
Great place just seconds from the beach! We arrived late (2 a.m.) from canceled fights and had trouble with the lock code. (User error) Someone answered my call immediately and got us right in. There’s beach supplies such as a wagon, chairs, umbrella and even towels, which were so convenient. I highly reccomend this place! Great stay!

Siesta Key Villa with beach to bay access.
My boyfriend and I were extremely pleased with this location. It had everything we needed and more. We always took the Frog Hop to and from the village. The access to the pool and beach was an easy walk. The beach was not crowded and was the perfect distance away from the main crowd. If I ever travel back to Siesta Key, I will absolutely be staying in the same location.

VIlla Venice
This home is absolutely stunning if you’re looking for a getaway with your family or evening another couple. The home is very spacious, the pool is absolutely stunning and perfect and the beach is just a short drive away! Very local to many things! Bonnie was so sweet and quick to respond to whatever we needed! Would recommend this place to anyone !

Robinhood Beach Villa near Siesta Key Beach!
We had trouble with our flight so we arrived in the middle of the night. That was no problem for Chad and his team. It was easy self check-in. When we had questions there was a quick respond. The house was very convenient and had every thing to make a nice meal. Thank you Chad en team!

2025 Remodeled private villa, 6 min walk to beach
Colleen’s accommodations included all the comforts of home. We truly enjoyed our 8 day stay. Colleen is a great host and we highly recommend doing business with her.

Mi Pequeña Casa - 2/2 on a lake
Verushka es la mejor anfitriona!!! Es la segunda vez que nos hospedamos con ella. Sin duda la volveríamos elegir! Todo limpio, cómodo, todo impecable!!!

Welcome to Casa Covella in Polynesian Gardens
We had a great vacation at Joe's place! It was super convenient to get to and close to Costco and grocery stores. The house was in great condition, and lots of fun for the family! The house is on Crescent Beach, which is beautiful. There were beach towels, chairs and a wagon. The public beach access is about a half a mile walk from the home. You are not able to access the beach across the street because of private condos with gated entrances. That is the most difficult thing about a lot of Florida beaches. We would happily return to this house again! The neighborhood was quiet and well-maintained!

CT Villa
Wonderful place to stay. Everything is nice and new and clean. Great value. The neighborhood was very nice and quiet as well. This is the place to book.
Quick stats about villa rentals in Siesta Key
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ588 before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
60 properties are a good fit for families
Rentals with a pool
100 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- John's Pass
- Crescent Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Raymond James Stadium
- North Beach
- Vinoy Park
- Coquina Beach
- Manasota Key Beach
- Tampa Theatre
- Fort De Soto Park
- Curtis Hixon Waterfront Park
- Streamsong Resort
- Jannus Live
- Myakka River State Park
- Splash Harbour Water Park
- River Strand Golf and Country Club
- Lakewood National Golf Club
- Alafia River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- North Beach At Fort DeSoto Park