Vacation rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Siesta Key rentals with a pool

House rentals with a pool

Top guest favorite
A heated pool with a curved shape is surrounded by a screened patio, featuring lounge chairs positioned for relaxation. A spacious covered area showcases seating and dining options, with views of lush greenery and wooden fencing providing privacy.
Home in Sarasota
4.97 out of 5 average rating, 241 reviews

Your private retreat near Siesta Key Beach.

PaoloRating, 5 stars3 weeks ago
Excellent location, just a 10-minute drive from the beach. The house is spacious, very comfortable, and has everything you need for a relaxing stay. The pool area is beautiful and perfect for cooling off in the heat. We had a great time and would gladly return!
Top guest favorite
A spacious heated saltwater pool is surrounded by lounge chairs and umbrellas, situated in a sunlit area with palm trees and greenery. The clear blue water reflects the blue sky, creating an inviting atmosphere for relaxation.
Home in Sarasota
4.98 out of 5 average rating, 161 reviews

New remodel- 150 Yds to Beach and Restaurants!

LisaRating, 5 stars1 day ago
This is our 3rd time staying here and I plan to keep going back. The home is beautiful, clean, comfortable and has everything you could need. The location is perfect! It’s our favorite vacation spot!
Guest favorite
The exterior of the home showcases a one-story structure surrounded by a well-kept lawn. A covered parking area is present, alongside vibrant landscaping featuring various plants and trees. Clear blue skies create a bright and welcoming atmosphere.
Home in Sarasota
4.94 out of 5 average rating, 152 reviews

La Hacienda / heated pool, hot tub, 6 mi to beach

CarlynRating, 5 stars3 weeks ago
Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.
Guest favorite
The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.
Home in Sarasota
4.88 out of 5 average rating, 156 reviews

5 minutes to private Siesta Key Beach + 2 pools

DonnaRating, 5 stars1 month ago
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!
Top guest favorite
A serene private pool area is framed by lush greenery and palm plants, with a view of a white fence. Two blue Adirondack chairs sit on the grass beside the pool, inviting relaxation under the sun.
Home in Siesta Key
5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

ZacharyRating, 5 stars1 month ago
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!
Guest favorite
A screened enclosure surrounds the pool area, offering protection while allowing light to filter through. Tropical plants are positioned along the perimeter, complementing the spacious pool deck. Two lounge chairs with teal cushions are placed nearby, providing a relaxing spot for sunbathing.
Home in Sarasota
4.95 out of 5 average rating, 213 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

LisaRating, 5 stars1 day ago
We loved our stay! The home was just as described. It was very clean and had everything we needed for a comfortable stay. The property is a short drive from first class Siesta Key and other beaches. Romualda was an amazing host. She responded quickly to our questions and went out of her way to make us feel at home. I highly recommend!!
Guest favorite
A private pool area is framed by lush tropical landscaping, featuring palm trees and vibrant plants. Comfortable lounge chairs are positioned beside the inviting blue water. A boat dock can be seen in the background, offering scenic views of the bay.
Home in Sarasota
4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

CourtneyRating, 5 stars1 month ago
This was among the most beautiful and well-appointed Airbnbs that we’ve had the pleasure of staying in! Our trip was centered around a family 60th birthday celebration and this was such a lovely backdrop for our gathering. Our primary plans were to enjoy the sunrises and gorgeous outdoor area, cooking meals on the grill and enjoying them by the pool with a view of the intercoastal waterway. As such, when we arrived to find that the grill wasn’t working properly, we were disappointed. We communicated with our host about the grill the day after our arrival, and received an immediate response. However, it ultimately required back and forth texts (some at our initiation due to not receiving an update) and three days until the handyman graciously brought over his grill to loan us. Something we learned from this trip is the importance of communicating to your hosts what it is about their place that is most important to your stay—and perhaps we should have checked on the grill specifically.
Top guest favorite
A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.
Home in Sarasota
4.98 out of 5 average rating, 105 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

MattRating, 5 stars3 weeks ago
Great place, very clean and had everything we needed. Instructions very clear and the pie waiting for us in the fridge was much appreciated! The beach gear was a nice touch, just a pity the weather wasn’t kind to us.

Condo rentals with a pool

Guest favorite
The open-concept kitchen and dining area feature modern furnishings, with a spacious table for six and bar seating along the kitchen island. Floor-to-ceiling windows provide unobstructed views of the beach, allowing natural light to brighten the room.
Condo in Sarasota
5 out of 5 average rating, 8 reviews

Stunning Siesta Vistas Direct Beach Access & Pool

JenniferRating, 5 stars2 weeks ago
Amazing views!!! What a beautiful condo! We are so happy we stayed here! Pros: Very very clean, fresh and new. Plenty of towels, both bath towels and beach towels. Beds were comfortable. Kitchen was stocked nice. The pool was very nice, easily accessible, and there was a restroom in the adjacent tower for us to use. Extra toilet paper in bathrooms, extra paper towels in kitchen, and a couple laundry pods. Cons: Washer/Dryer was a one unit combo machine which was tiny. We needed to dry our beach towels because it rained while were there and could not use the unit in the condo. There are pay washers and dryers on the first floor of the tower that we had to use instead. The living room and master had cable which was a pro but the living room had a Roku that wasnt signed in so we couldnt use that. There were no scissors in the kitchen which seems insignificant until you need them. Shark teeth = drive south to Caspersen beach!!!! We did not find any at this beach
Guest favorite
A tranquil pool area is surrounded by lush greenery, with gentle palm trees swaying in the breeze. Lounge chairs are positioned alongside the clear blue water, while bright red umbrellas provide shade. Sunny skies add a bright atmosphere to the inviting scene.
Condo in Siesta Key
4.93 out of 5 average rating, 205 reviews

Steps away from beach and village! #1 in Siesta!

ChristianeRating, 5 stars5 days ago
This is one of the best Airbnbs I have ever stayed in. It is perfect if you have young children. It was just me and my daughter (age 2) for the week. She loves the bunk beds and there was a stroller we used all week. The private pool is so nice and shared among the 6 condos but we had it to ourselves several times throughout the week. The beach is about an 8 minute walk from the condo. Everything you need is down the street and major grocery chains are all within 15-20 minutes. VK was super responsive and kind - this one is going in my favorites and we will definitely be back. Highly recommend!!
Top guest favorite
A comfortable living area features a neutral sofa with decorative cushions, flanked by two bedside tables with lamps. A piece of wall art depicting a beach scene adds a calming touch, while a ceiling fan provides overhead cooling. Natural light is visible through an open doorway.
Condo in Siesta Key
4.92 out of 5 average rating, 239 reviews

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky

KassandraRating, 5 stars1 week ago
Such a beautiful stay with all the amenities, clear instructions and a clean place with everything you need surrounding you. Beautiful home, I appreciate the stay!
Guest favorite
Condo in Siesta Key
4.98 out of 5 average rating, 40 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

PaulaRating, 5 stars1 month ago
We have been coming to Siesta for years and rented all over the key. Siesta Dunes is right on the beachfront. It’s large with a huge pool in the centre with tons of loungers and umbrellas and then you walk out to the massive beach. Although people say walkable to the beach, in most cases you have to cross the main road and go to the other side which is a severe pain. This is all contained and it’s important for me to have the least work possible on vacation. There’s a centre deck with bbqs overlooking the beach where everyone comes to watch the sunset. Tanya’s place is bigger than it looks on the photos with two back decks, plenty of seating inside and back out. Siesta is our home twice a year and now that we found Siesta Dunes we are booked for Christmas. The trolley is the best part of Siesta outside of the massive white beach and we always make a date night at Summer House. Tanya’s is worth staying at.
Superhost
A two-story building with a light yellow exterior is situated among palm trees and lush greenery. The entrance features a covered porch, and the pathway is lined with flowering plants, leading to the parking area and common spaces.
Condo in Lido Key
4.8 out of 5 average rating, 104 reviews

LIDO KEY 1 BR/1Bath Heated Pool 16

ChrisRating, 5 stars9 months ago
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed
Guest favorite
A spacious swimming pool is surrounded by palm trees and lounge chairs, reflecting clear blue skies. The pool area is well-maintained, and the building's balcony overlooks the pool, providing a serene atmosphere for relaxation.
Condo in Siesta Key
4.9 out of 5 average rating, 119 reviews

Crystal House on Siesta Key Beach

BiancaRating, 5 stars1 week ago
We loooved it here! The space was perfect for our family. I cooked several meals and the kitchen had everything I needed. The location was convenient to grocery stores and walking distance to local restaurants and ice cream shops. The trolley stop is right at the resort so very convenient free rides to downtown Siesta Key was one of the highlights of our trip. We also grilled in the back of the resort by the bay which was nice! Oak trees all around. The pool was perfect temp. The fob didn’t work for one of the gates but there were three others we were able to get in without issue. The beds and pillows were soooo comfy. The ONLY issue we had was from the pics on the original post it appeared the walk to the closest public beach access was 2 min but it was actually 15. In the Florida heat that was rough but we pushed through! Oh and last thing, the scooters were a hit with everyone in our family. So much fun! 😆 Thank you so much for giving us an amazing stay!!
Guest favorite
A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.
Condo in Sarasota
4.86 out of 5 average rating, 149 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars3 weeks ago
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!
Guest favorite
The outdoor pool area features a clear blue pool surrounded by lounge chairs and shaded tables. Bright turquoise umbrellas provide shade over the tables, and a thatched-roof structure is visible nearby. Lush palm trees and the serene intercoastal waterway create a peaceful backdrop.
Condo in Siesta Key
4.85 out of 5 average rating, 155 reviews

The Key to a Great Vacation!

JillRating, 5 stars1 day ago
Cute, cozy condo. Close to everything on Siesta Key, and walkable to the private beach. Jen was great to work with & very responsive with communication. Affordable unit & the ability to have free cancellation up until a week before the date was a big relief as we had many potential factors leading up to the trip. Thankfully it all worked out & we were able to take our vacation & had a fabulous time!

Quick stats about vacation rentals with a pool in Siesta Key

  • Total rentals

    1.4K properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    24K reviews

  • Family-friendly rentals

    1.2K properties are a good fit for families

  • Pet-friendly rentals

    210 properties allow pets

  • Rentals with dedicated workspaces

    670 properties have a dedicated workspace

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