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Villa vacation rentals in Siesta Key

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Popular amenities for Siesta Key villa rentals

Private villa rentals

Villa in Longboat Key
4.75 out of 5 average rating, 4 reviews

Waterfront Condo, Private Boat Dock, Beach Access!

PeterRating, 5 stars1 week ago
loved staying at Val's place. a great, private location in walking distance of the beach and delicious restaurants. a very cute park right next to the unit. would stay again
Superhost
Villa in Sarasota
4.74 out of 5 average rating, 19 reviews

Tiki Bella Villa (Entire home with Pool)

JanaeRating, 5 stars11 months ago
The home was as described. We really enjoyed the pool, and everything we needed was there. Our dog loved the fenced backyard too. The mattresses were very comfortable. While we were a little hesitant about plane noise after our arrival, the air traffic didn’t interrupt our sleep or fun at all. Highly recommend Gina’s listing, and we would definitely stay there again.
Villa in Sarasota
4.89 out of 5 average rating, 9 reviews

Remodeled Mid-century POOL house

MelanieRating, 5 stars1 week ago
Aurelia was very responsive and helpful before and during the trip. The home was clean and felt very welcoming. However we did end up purchasing some standing fans for a couple of the rooms as it got very hot and there wasn’t much airflow in the house. Overall we really enjoyed our stay and our daughter had a blast in the pool!
Guest favorite
Villa in Siesta Key
4.93 out of 5 average rating, 15 reviews

2025 Remodeled private villa, 6 min walk to beach

BruceRating, 5 stars2 months ago
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.
Superhost
Villa in Bradenton
4.75 out of 5 average rating, 102 reviews

My Little House - 2/2 on a lake

MichaelRating, 5 stars3 weeks ago
We had a great stay. My wife and I had a great time in the area and this listing was centrally located to everything we wanted to do. House was updated and very clean! Will definitely be staying here again!
Villa in Holmes Beach
4.71 out of 5 average rating, 7 reviews

Modern 3BR 2nd-Floor | Balcony | Pool

WendiRating, 5 stars19 months ago
The condo was beautiful and actually larger than I expected. Sometimes the photos are deceiving regarding the size of rooms and this condo is spacious and open. 5 minute walk to the beach. Quiet neighborhood. I would definitely return to this condo for future visits to AMI.
Villa in Siesta Key
4.82 out of 5 average rating, 11 reviews

Welcome to Casa Covella in Polynesian Gardens

ErikaRating, 5 stars1 month ago
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!
Superhost
Villa in Sarasota
5 out of 5 average rating, 19 reviews

Villa Siesta, Secret Downtown Treasure-heated Pool

HopperRating, 5 stars87 months ago
great location. great community with friendly & helpful residents. made lots of friends. May consider buying here.

Luxury villa rentals

Guest favorite
Villa in Sarasota
4.97 out of 5 average rating, 34 reviews

Luxurious 4-Bedroom Retreat with Pool

AuraRating, 5 stars2 days ago
The house is beautiful and well maintained. It has all the amenities, it's comfortable and modern. There were some details that we noticed when we arrived, we communicated them and the next day the manager quickly corrected the details. We really recommend it 100%.
Top guest favorite
Villa in Holmes Beach
5 out of 5 average rating, 17 reviews

Waterfront in Paradise

JulieRating, 5 stars2 months ago
We had an amazing stay at Mimi’s! I’ve never communicated so much with a host but she was just so helpful and willing to answer any and all questions! It felt like I was staying at a friends’. We loved our accommodations and I’m picky! Everything was well thought out, super clean and very cozy! The view to the harbor was awesome and our fishing excursion picked us up right at our dock! We loved our stay and would highly recommend! Mimi will make sure everything is perfect!
Guest favorite
Villa in Sarasota
4.92 out of 5 average rating, 53 reviews

Siesta Key Palm Paradise w/ Heated Salt Water Pool

JenniferRating, 5 stars1 week ago
First time in Florida and what a wonderful house we got to stay at. The house is so beautiful we all loved the pool. Very quiet neighborhood. It’s just a couple miles away from Siesta Beach. Lots of local restaurants near by. We will definitely be back.
Guest favorite
Villa in Siesta Key
4.9 out of 5 average rating, 168 reviews

Mermaid Villa Ocean Front!

TiffanyRating, 5 stars2 weeks ago
We’ve stayed MANY places in Siesta…. It’s my favorite place to visit. This condo is definitely at the top of my list and I will be back! Beautiful, great location, and one of the cleanest AirBnB I’ve ever stayed in. Really a great experience!
Superhost
Villa in Holmes Beach

La Isla Bonita by Coastal Chic Vacations

ElizabethRating, 5 stars2 months ago
The house is roomy and had plenty of space for everyone, including multiple eating spaces and nice outdoor areas, especially the breezy top floor porch with nice water and sunset views. It's truly a 5-minute max walk or 2-minute drive to a busy beach with amenities (cafe/outdoor showers/restrooms), or a 10- to 15-minute drive to the less-busy/fewer amenities beaches at the island's northern and southern ends. Also that same 2-minute drive to the grocery, two drug stores, and several restaurants. While close to a main road, at the house and even outside it was strikingly quiet and serene. The pool was nice and the game room was great to have. My one suggestion would be the addition of a designated sand-wash-off spot/hose at the front of the house near the driveway.
Guest favorite
Villa in Sarasota
4.95 out of 5 average rating, 40 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

KateRating, 5 stars1 week ago
We had a wonderful time during our mini family reunion! The house was perfect for our group, including a 1.5-year-old and a dog. The splash pad was an absolute hit and kept everyone entertained. The Siesta Suite was also a plus for my brother, his wife, and their daughter. The location is also great—just 10–15 minutes from restaurants and downtown. The only downside was the bunk bed room; the mattresses there were uncomfortable and the room got quite warm. That said, all the other bedrooms had very comfortable beds and stayed nice and cool. Overall, a great stay!
Superhost
Villa in Osprey
5 out of 5 average rating, 11 reviews

Paradise with a pool, pier and private beach area

LauraRating, 5 stars18 months ago
Beautiful house! Lots of room for everyone, sparkling clean! Fantastic location. Perfect for our family gathering.
Top guest favorite
Villa in Siesta Key
5 out of 5 average rating, 9 reviews

Siesta Key at Sunset-Top Floor

ShannonRating, 5 stars1 week ago
Gorgeous home with a well-appointed kitchen. The hosts did an amazing job decorating the space & providing anything you could possibly need. When you walk in the door a very yummy ‘Welcome Basket’ is waiting for you with local goodies. Stop by Crescent Beach Market if you need more of the chips/salsa! Eating breakfast on the front porch is such a great way to start the day. Then you can walk to your private beach access and enjoy the white sand. There is everything you need for a beach day waiting for you in the garage. When you are ready to head back - take a nap on the super comfortable rocking lounge chairs or curl up in the soft blankets on the reclining sectional. This rental is a gem! Sharing the space with the guests downstairs wasn’t an issue for us bc of different schedules. If you have friends/family who like to vacation together but still want separate spaces renting out both the lower and upper units would be perfect. Must Go Places: Made In Rome Organic Gelato, Spearfish

Villa rentals with a pool

Villa in Holmes Beach
4.82 out of 5 average rating, 34 reviews

Beautiful Islands West Resort - Villa #6 Starfish

KathyRating, 5 stars16 months ago
This is our second year going to the West Island Villas. There is a few of us that agreed to return at the same time. We all had a great time together and did again this time. Social and fun. Add great weather and location it’s a win.
Villa in Bradenton Beach
4.75 out of 5 average rating, 4 reviews

Starfish East- Beautiful Villa with amazing

SueRating, 5 stars19 months ago
This was a sisters vacation….and we couldn’t have asked for a better place to spend it. The home was beautiful and right near the beach. The pool was private and clean. We loved the feeling every time we walked in the door. We walked to dinner and shops and coffee. And any questions were answered right away. Can’t wait to come back.
Villa in Siesta Key
5 out of 5 average rating, 3 reviews

Siesta Key Beach Villa

DanielRating, 5 stars24 months ago
close to white sugar powder sand beaches, shops, grocery stores. the security was top of the line friendly and professional. awesome location. Cold A/C. hot showers. nice screened in pation. Zero complaints, we will be back again. thank you for letting my family borrow your residence for a week!
Villa in Anna Maria
5 out of 5 average rating, 4 reviews

Bean Point Residence Unit B by SeaBreeze Vacation

JanetRating, 5 stars8 months ago
This place was wonderful. Best part..the pool and the location to the beach. You could easily walk back to the house from the beach if you forgot something. Easy to run out to see the beautiful sunsets. The pool was awesome. We used it a lot. So nice to have all of the provided amenities including beach towels, beach wagon, beach chairs, umbrellas, shampoo, soap, etc. paper towels, laundry pods, dishwasher pods. Could have used a few things like salt and pepper in the kitchen but they were very generous with the amenities. The area is quiet with just a little traffic going by. The place was VERY clean. Only thing to know which didn't bother us is the laundry room is off one of the bedrooms so if doing laundry at night it's pretty loud, and you have to go through that bedroom to get to the pool. Again didn't really bother us but might depending on your situation. could also go ti pool from front. Close to Rod & Reel Pier for great lunch. about 15 min walk to shuttle and Pine Ave.
Guest favorite
Villa in Siesta Key
5 out of 5 average rating, 16 reviews

Siesta Key Villa with beach to bay access.

AlainaRating, 5 stars11 months ago
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 in Venice
5 out of 5 average rating, 7 reviews

VIlla Venice

MeganRating, 5 stars2 months ago
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 !
Villa in North Port
5 out of 5 average rating, 4 reviews

Family pool home near beaches & golf. May-June

TressaRating, 5 stars1 month ago
Absolutely all around wonderful experience for our family of four and our dog. We all felt welcome as if we were staying at a family members vacation home. They have everything you need, and several added touches to enhance your stay! Cleanliness, location to golf courses, lit walking path, heated pool, large seating areas/tables, decor, supplies provided and kind hosts all helped make our stay perfect. Lisa and Jeff were accommodating, kind, responsive and caring- will definitely rent from them again, highly recommended!
Villa in Holmes Beach
4.5 out of 5 average rating, 8 reviews

Welcoming 3BR 2nd-Floor | Balcony | Pool

SabriyaRating, 5 stars53 months ago
Beautiful space, modern decor & high end linens. Exceptionally clean, great location, 8 minute walk to gorgeous beach.

Quick stats about villa rentals in Siesta Key

  • Total rentals

    100 properties

  • Nightly prices starting at

    G$33,571 GYD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. Villa rentals