
Villa holiday rentals in Siesta Key
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Top-rated villa rentals in Siesta Key
Guests agree: these villas are highly rated for location, cleanliness and more.
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Popular amenities for villa rentals in Siesta Key
Private villa rentals

Canal Front 3-Bedroom Grand Villa with Pool
Absolutely LOVED our stay! Host and owners were VERY responsive, even during a minor issue at check in, they responded and had it resolved extremely fast. Very clean, comfortable, neighbors were so friendly, we felt very safe, this place made our girls’ weekend PERFECT! And the salt water pool?! Chef’s kiss!!!! We loved it!! Thank you so much for having us and allowing us to enjoy this little slice of heaven in Florida!

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!

Tiki Bella Villa (Entire home with Pool)
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.

Florida Villa Sunrise - 4 Bedroom Home with Pool
This home was everything that was promised. It was huge. My family were able to check in a few hours early which really sweetened the deal. The home really suited my family needs. There were toys and strollers, beach toys, and bikes. It was awesome! Will definitely come back next year!

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.

My Little House - 2/2 on a lake
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!

Your own tropical paradise in Sarasota
We absolutely loved our stay here. Anna was friendly and helpful. The house was spotless, comfortable, and had everything that was needed. The location was unbeatable. Will definitely return! Thank you Anna!

River Pointe 3/2 Lakefront Home with Heated Pool
Immediately upon arrival, I thought that the pictures did not do this place justice. It was clean, spotless, and very well stocked this house had everything we could possibly need and even things we didn’t even think we needed it, but had available. We enjoyed the location being fairly close to the beach yet private and away from The madness of the tourists. We really enjoyed sitting in the pool or on the back patio and watch all the wildlife, especially the birds coming and going. It was peaceful, relaxing, and everything we needed to get away from the Midwest for spring break. Thank you so much to the host For staying in communication and being so great.
Luxury villa rentals

Private Beach Villa | Charming Decor | Sunset View
A++++ stay! Felt so lucky to be the inaugural renters of this beautiful property, which had all the amenities, cleanliness and professional caretaking of a top-flight rental, but still somehow felt like a home. HUGE house, perfect for a family with lots of privacy and space for everyone. The private access beach is a rare and unbelievably luxurious plus, and the house comes equipped with warm-water outdoor shower, beach chairs and umbrellas and to help you make the most of it. One of the best-stocked kitchens I've ever seen, with every possible kitchen accessory and super-sharp knives. The managers / owners were very responsive, gracious and helpful -- definitely pros. An idyllic, peaceful getaway, tucked away in your own private corner of Gulf Coast Florida . . . Highest recommendation.

Luxurious 4-Bedroom Retreat near Siesta Key
This property was fantastic! Located in a great spot near shopping and restaurants, it made exploring Siesta Keys so convenient. The host was incredibly responsive and attentive, which made our stay even more enjoyable. The home was well-equipped with everything we needed, including beach chairs, beach towels, a large cooler with wheels, and a cart with wheels—perfect for days at the beach! We absolutely loved the patio and pool area; it was the perfect place to relax after a day of exploring. I would highly recommend this property to anyone visiting Siesta Keys and would definitely stay here again on our next trip. Truly a wonderful experience!

Relaxation awaits in this bohemian inspired villa
Christine's home was amazing and it was the perfect size & space for our family. My family enjoyed the pool and didn't ever want to get out. The property was close to Lido Beach & Siesta Beach, which we enjoyed both. We actually extended our time for a couple more days with no issues. Thank you Christine so much for having your home available for our family to enjoy and if we ever look into having another AirBnB, we definitely will book. I will also tell others if they are looking for an AirBnB in the Sarasota area.

Mermaid Villa Ocean Front!
This is the perfect spot in Siesta Key! Across the street from the beach and walkable ro the village. Would come back to Barb's place every time. Ten stars!

La Isla Bonita by Coastal Chic Vacations
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.

Paradise with a pool, pier and private beach area
Beautiful house! Lots of room for everyone, sparkling clean! Fantastic location. Perfect for our family gathering.

Calico AMI – Steps to Sand, Family Paradise!
My husband and I, along with our two daughters, son in laws and 17-month-old granddaughter had a wonderful stay at Calico. The house was stocked with everything you could possibly need and was in a great location. We enjoyed the pool, the fun games and were so grateful for the supply and use of all the beach equipment. Celine was a great host, very responsive and quick to answer any questions we had. Thank you Celine for all the helpful tips, the amazing guidebook and sharing your beautiful home with us. It was our first time visiting Anna Maria Island and we can’t wait to come back!

Cheerful 4-bedroom Villa with heated pool.
A beautiful place set up with a nice pool area. As soon as we walked in everything smelled clean.
Villa rentals with a pool

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.

Remodeled Mid-century POOL house
Thank you Aurelia! We loved your place. A small issue we had was quickly resolved. Lovely pool, comfy beds. Great place to stay while attending Youth Nationals Rowing Champs at Nathan Benderson. Will definitely return in the future.

Waterfront Villa with heated Pool
Amazing stay! Very private, gorgeous property. Our local contact was very responsive. It’s worth the stay just being next to the water and watching the wildlife! Would 100% stay again!

Dolphin Cove Waterfront St. Pete Beach w/ Pool
My parents and I and our 3 dogs absolutely loved our stay here. We enjoyed the back yard and pool more than we enjoyed going to the beach! The house was extremely clean, and we loved the huuuuge TV in the living room. The kitchen is pretty bare bones as far as cooking and cleaning items, but that was a minor issue for us. My dad said he wanted to come back to this house at least 20 times haha. We'll be back!

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.

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!

Luxury waterfront in the heart of treasure island
Great location and space

Villa Siesta, Secret Downtown Treasure-heated Pool
great location. great community with friendly & helpful residents. made lots of friends. May consider buying here.
Quick stats about villa rentals in Siesta Key
Total rentals
100 properties
Nightly prices starting at
$206 SGD 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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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park