Villa vacation rentals in Siesta Key

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Popular amenities for Siesta Key villa rentals

Private villa rentals

Top guest favourite
Villa in Sarasota
4.97 out of 5 average rating, 59 reviews

SEALAND 3/2 Modern Villa w/ Pool near Siesta

SarahRating, 5 stars2 weeks ago
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!!
Guest favourite
Villa in Rotonda West
5 out of 5 average rating, 20 reviews

Spacious Home with Heated Pool Near Beaches

KatRating, 5 stars2 days ago
The house was absolutely beautiful and stunning. I loved everything about staying there. It was very peaceful. I look forward to staying again in the future. I also live the proximity to the beaches.
Superhost
Villa in Bradenton
4.87 out of 5 average rating, 97 reviews

Florida Living

CallahanRating, 5 stars2 weeks ago
Had a great stay at this clean and relaxing property! The pool was great and everything met or exceeded expectations.
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 stars1 month 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 South Gulf Cove
4.77 out of 5 average rating, 47 reviews

Brand New! Fabulous Paradise 3 b/ 2 bath Villa

SueRating, 5 stars1 month ago
We thoroughly enjoyed our stay at Sandra’s beautiful home and really feel lucky….as well as blessed to have spent a month there! We loved our daily routine starting with walks in the quiet neighborhood and later relaxing by the pool. We visited our favorite beach on Boca Grande several times….with many gorgeous sunsets! If you are lucky enough to spend any time at Sandra’s I’m positive you’ll feel the same. The location is excellent for any day trips you may want to take. The house itself is very comfortable….and rest assured you won’t find anything she has forgotten! We are hoping to stay again…for now we’ve got great memories!!
Villa in Sarasota
4.75 out of 5 average rating, 28 reviews

Lovely Family Villa In Paradise!

AnnaRating, 5 stars23 months ago
We really loved the house. It was clean and exactly as described. We are a family of 3. The area feels very safe. The community is kind and well maintained. There is almost no traffic around the house. We had a good night sleep, because there was no noise or alarms. We had a 15min drive to Siesta Key Beach which has a lot of free public parking and good restrooms. Its also 15min to I-75. In the garden you can watch lots of birds, rabbits and squirrels. The kitchen has everything you could need for cooking and dining. The washer and dryer is also located in the kitchen and worked well. There were also lots of towels, vacuum cleaner, hair dryer, drying rack, fast internet, tv with streaming box, toys, cooler, a drawer with essentials like batteries and yarn. In the garage you find a lot of beach stuff like poolnoodles, chairs, umbrealls and more toys. Check in and check out was very easy.
Guest favourite
Villa in Rotonda West
5 out of 5 average rating, 15 reviews

Charming,Spacious 4/2, Heated Pool with Canal View

DanaRating, 5 stars1 month ago
Myself and another family shared this home for our spring break trip and it was perfect for us. Definitely the best part of the home was the pool and pool deck area. It was a great size, super clean and the outside furniture was great! The home itself was spacious and super well appointed not only in the kitchen but bathrooms as well. We enjoyed being only 25 minutes from Boca Grand/Gasparilla Island to get to a beautiful beach. Having 2 rooms with king beds was a bonus too. We did not find the pullout couch to be a viable 4th bedroom however. Although we had to use it, it wasn't a comfortable bed and the doors didn't close for privacy. The owner/manager was super responsive to all our questions and concerns. We would stay here again if we were in the area.
Guest favourite
Villa in Englewood
4.93 out of 5 average rating, 120 reviews

Unwind at Casa Blu: Sun, fun, pool, close to Beach

CynthiaRating, 5 stars2 weeks ago
Nice house in a quiet neighborhood. Perfect for relaxing in the pool.

Luxury villa rentals

Villa in Bradenton Beach
4.75 out of 5 average rating, 4 reviews

Starfish East- Beautiful Villa with amazing

SueRating, 5 stars18 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.
Guest favourite
Villa in Englewood
4.95 out of 5 average rating, 98 reviews

STUNNING 3/2 beach+pool property! 2 kings/2 bunks!

JenniferRating, 5 stars9 months ago
We loved staying here especially having the beach just a few feet away! Although there was construction taking place in the development, it did not interfere with our stay at all! We didn’t even notice the workers on site. If you get a chance to book this home, do it. April is an amazing host and has thought of every amenity possible! We look forward to booking again soon!
Guest favourite
Villa in Sarasota
4.97 out of 5 average rating, 29 reviews

Sarasota Luxury Pool Retreat Near Siesta

DavidRating, 5 stars1 month ago
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!
Villa in Holmes Beach
4.63 out of 5 average rating, 19 reviews

2 Bd, Islands West Resort - Villa #7 AMI Lime Fish

SaigeRating, 5 stars10 months ago
Super clean & in a great location. Very private, would definitely stay here again.
Villa in Sarasota
4.8 out of 5 average rating, 40 reviews

Relaxation awaits in this bohemian inspired villa

LexieRating, 5 stars1 week ago
We had a great week here! 3 families with lots of kids and it had everything we needed, space to spread out, plenty of room in the kitchen, and enough pool towels. Safe to say our kids spent more time in the pool than out! Thanks for sharing your home with us!
Guest favourite
Villa in Siesta Key
4.9 out of 5 average rating, 163 reviews

Mermaid Villa Ocean Front!

LizRating, 5 stars4 days ago
The mermaid villa was beyond our expectations. It was roomy enough for four adults, two bathrooms lots of stuff in the kitchen and the patio was gorgeous. It’s directly across the street from beach access and very walkable to the downtown area.
Guest favourite
Villa in Englewood
5 out of 5 average rating, 50 reviews

Ocean View Villa Manasota Key

KendraRating, 5 stars3 weeks ago
Fabulous location…pathway leads right to the beach. Lovely and quiet house well manicured and comfortable. Great new appliances in the basic kitchen. Looking forward to returning!!
Guest favourite
Villa in Holmes Beach
4.97 out of 5 average rating, 70 reviews

Calico AMI – Steps to Sand, Family Paradise!

SamanthaRating, 5 stars1 month ago
Céline's home was perfect for our family of 7. Celine was proactive in making sure we had everything we needed. She went the extra mile with details around the house for us to have a such an enjoyable stay. The house is walkable to a grocery store and the public beach. Sometimes you can hear traffic but she does an amazing job with the pool and waterfall to drown out the traffic and it makes you feel like you are in your own backyard oasis! We definitely recommend staying here. We absolutely loved it and can't wait to be back. Thank you for everything Céline!

Villa rentals with a pool

Villa in North Port
4.83 out of 5 average rating, 24 reviews

Cheerful 3-bed villa with heated pool+beach staff

AmyRating, 5 stars2 months ago
We really enjoyed our stay! The house was very clean, comfortable and had everything we needed. We really appreciated having the beach gear, including a wagon the transport everything. Very convenient! Beautiful beaches within 30 minutes. Wellen Park and Warm Mineral Springs worth checking out! Irina was very responsive. Pool temp was a little cooler than our comfort level and some of the outdoor things are a bit warn (basketball hoop broken, pool floats, etc.). Other than that the place was just perfect! Highly recommend!
Guest favourite
Villa in St. Petersburg
4.94 out of 5 average rating, 102 reviews

Heated Pool! Huge Walk In Shower! 5 min to beach!

DaveRating, 5 stars1 week ago
We thoroughly enjoyed our time at this home. After cooking delicious meals in the well stocked kitchen, we enjoyed our food outside poolside under the covered lanai. In addition, the beds are very comfortable. We enjoyed taking our dogs for walks through neighborhood.
Top guest favourite
Villa in Englewood
4.98 out of 5 average rating, 94 reviews

Coastal Retreat Villa with pool • near beaches

KarinaRating, 5 stars2 weeks ago
Family of four traveled to South Florida for the first time for spring break. We had an incredible time, location of the house is close enough to some beautiful beaches and cute little towns. The house itself is everything the description says. Very spacious and comfortable…the pool was a huge plus for my daughters, the water was very clean and warm. We loved the screened in porch, ate many of our meals out there and didn’t have to worry about bugs bothering us. We LOVED our stay at Yeb and Lubas place and will definitely come back!
Superhost
Villa in Seminole
4.94 out of 5 average rating, 66 reviews

Perfect location 6BR/4BA Pool GameRoom 5 min Beach

NancyRating, 5 stars2 weeks ago
We were a group of 13 women and had an awesome week! This place has lots of space and everything you need…for the indoors and outdoors. We spent a lot of time around the pool, which is in great shape and well maintained and we also drove to the beach several times (lots of beach chairs, towels, sun umbrellas, coolers etc and a wagon to transport everything in!). The house is very conveniently located if you want to go into Tampa (or take the Cross Bay ferry over to a Tampa Bay Lightning game…which we did!). We had a few issues when we first arrived but Colburn was very quick to respond and all was resolved in a very timely manner. We are planning to come back again next year!
Top guest favourite
Villa in Rotonda West
5 out of 5 average rating, 22 reviews

Florida lakeside home - south facing pool & deck

EmilyRating, 5 stars3 months ago
Great house. It’s very spacious and has everything you could possibly need. Clean and comfortable furniture and bedding. Felt very safe in the neighborhood and loved checking out the local nature.
Villa in St. Petersburg
4.8 out of 5 average rating, 128 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

LindseyRating, 5 stars2 days ago
We loved our short but sweet stay at this house! Beautiful property, stunning pool, awesome views. Perfect for a family to relax and unwind and have fun.
Superhost
Villa in Rotonda West
4.79 out of 5 average rating, 24 reviews

Beautiful home, heated pool & 5 miles from beach!

BlaiseRating, 5 stars2 months ago
ABSOLUTELY GORGEOUS HOME! Loved the interior design and the pool was clean and amazing. Private backyard! Host was very responsive and friendly. Would highly recommend this stay!
Top guest favourite
Villa in Bradenton
5 out of 5 average rating, 38 reviews

River Pointe 3/2 Lakefront Home with Heated Pool

MichelleRating, 5 stars3 weeks ago
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.

Quick stats about villa rentals in Siesta Key

  • Total rentals

    100 properties

  • Nightly prices starting at

    $221 CAD 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