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Villa holiday rentals in Siesta Key

Find and book unique villas on Airbnb

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Popular amenities for Siesta Key villa rentals

Private villa rentals

Superhost
Villa in Port Charlotte
4.79 out of 5 average rating, 34 reviews

Canal Front 3-Bedroom Grand Villa with Pool

JenniferRating, 5 stars2 weeks ago
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!
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.
Guest favourite
Villa in Gulfport
4.88 out of 5 average rating, 80 reviews

Cozy funky duplex with KING bed

SalvadorRating, 5 stars4 weeks ago
Logement très pratique pour un couple ou solo, petit et cosy bien aménagé et équipé, super literie spacieuse et pleins de petites attentions pour un très bon confort et séjour, salle de bain et douche spacieuse. l’hôte Amanda est très réactive et disponible sur chaque demande ou sollicitation (demande de fer à repasser + planche disponible à notre arrivée 🤩), je recommande vivement ce logement et hôte pour votre séjour à Gulfport FL.
Villa in Sarasota
4.91 out of 5 average rating, 11 reviews

Remodeled Mid-century POOL house

SerenaRating, 5 starstoday
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.
Villa in St. Petersburg
4.77 out of 5 average rating, 138 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

TereonRating, 5 stars2 weeks ago
Great place to stay, will say it was missing the most random stuff like a broom to sweep floors/cleaning supplies. Trash bags and things like that. I left my box of trash bags and a broom there hoping the next guest can catch a break but the home was great neighbors were nice. No problems at all
Superhost
Villa in Bradenton
4.75 out of 5 average rating, 102 reviews

Mi Pequeña Casa - 2/2 on a lake

MichaelRating, 5 stars1 month 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!
Guest favourite
Villa in Treasure Island
4.88 out of 5 average rating, 17 reviews

Luxury waterfront in the heart of treasure island

Donal FrancisRating, 5 stars3 weeks ago
Great location and space
Guest favourite
Villa in Sarasota
4.83 out of 5 average rating, 53 reviews

Your own tropical paradise in Sarasota

MayaRating, 5 stars2 months ago
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!

Luxury villa rentals

Villa in Holmes Beach
4.84 out of 5 average rating, 63 reviews

Exclusive Islands West Resort - Villa #3 Seahorse

JimRating, 5 stars1 month ago
We stayed in seahorse number three a one bedroom bungalow. The place was spotless. Upon arrival they provided a beach wagon with two chairs towels, and even though I didn’t ask for them they were two beach bikes there waiting for someone.
Villa in Sarasota
4.81 out of 5 average rating, 42 reviews

Relaxation awaits in this bohemian inspired villa

MendyRating, 5 stars2 weeks ago
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.
Guest favourite
Villa in Siesta Key
4.9 out of 5 average rating, 168 reviews

Mermaid Villa Ocean Front!

TiffanyRating, 5 stars3 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 favourite
Villa in Sarasota
4.95 out of 5 average rating, 41 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Kathleen & AnthonyRating, 5 stars1 week ago
Easy check in and easy to find. Close to Sarasota beaches!
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.
Guest favourite
Villa in Holmes Beach
4.97 out of 5 average rating, 72 reviews

Calico AMI – Steps to Sand, Family Paradise!

EricaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Villa in Siesta Key
4.94 out of 5 average rating, 16 reviews

Siesta Key at Sunset-Lower Floor

StephanieRating, 5 stars3 weeks ago
This place was even better than what we imagined. This beach is a yearly tradition for us and now a stay at this property will also. The beach is the best and the house is so comfortable and meticulously set up. Our kids had a blast. The property is simply amazing. We will definitely be coming back.

Villa rentals with a pool

Villa in Anna Maria
5 out of 5 average rating, 5 reviews

Bean Point Residence Unit B by SeaBreeze Vacation

JanetRating, 5 stars9 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 favourite
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.
Guest favourite
Villa in Port Charlotte
4.79 out of 5 average rating, 39 reviews

Waterfront Villa with heated Pool

CoryRating, 5 stars1 month ago
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!
Villa in Sarasota
5 out of 5 average rating, 3 reviews

2bed/2bath steps away from Siesta Key beach!

JasonRating, 5 stars2 months ago
Everything was as described, outstanding experience.
Guest favourite
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.
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.
Guest favourite
Villa in Sarasota
5 out of 5 average rating, 8 reviews

Beautifull 2br villa, Sarasota

JohnRating, 5 stars5 months ago
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

Quick stats about villa rentals in Siesta Key

  • Total rentals

    100 properties

  • Nightly prices starting at

    $266 NZD 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