
Holiday rentals with a pool in Sarasota
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sarasota
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sarasota rentals with a pool
House rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
A beautiful home with a private, relaxed atmosphere and all the amenities you could need.

Charming Home in Sarasota-8min from Siesta Key
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!

Lake Front House with a Pool
This house was spotless, organized and had a loaded kitchen! It is in a amazing location near the beaches and the house came loaded with beach equipment. I would love to come back. Birute was very helpful with us and responsive in timely manner Thansk for all!

White Sands Villa - Heated Pool/Spa - Near Beaches
We had a great stay at this property. Seaglass Management was always responsive and accommodating. The house was clean and the backyard was large and well maintained. The only downside was the bathroom situation. There is no master bathroom and one of the bathrooms for the house is really a 3/4 bath. For 8 adults and a baby the bathroom situation was a little difficult, but we made it work.

NEW hideaway, Saltwater Pool&Spa, 10min to Siesta
I will definitely go back and stay here again when in Sarasota. The new beautiful modern pool and hot tub area is amazing was so tranquil and well thought out with high end lounging/seating for 10+. I spent most of my free hours around the pool area when at the house. WIFI was great when needing to work. The location was an easy drive to the local restaurants and quaint downtown area 5-10 min., to the closer beaches 15 -30 min., was bicycle/walkable for me (I am 65 y/o). I was in town for a conference and also saw alot of people on nearby small/clean little open air trolley-like buses getting around downtown (might want to check those out). I felt safe and walked/explored to the downtown hotel area (~ 40 min.). So close to the convenient Sarasota/Bradenton airport (~20 )! The hosts were so responsive and genuinely caring, they anticipated my needs before I asked by offering suggestions and options, so worth the stay! Thank you to the hosts!

Cozy Coastal - 2bd/2bath with Heated Pool and Spa!
Great location! So close to many different beaches and restaurants. The private pool area was our absolute favorite!

Cottage On Bay (private backyard, near beaches)
My husband, son and I loved staying at this gorgeous property. The interior is adorably decorated and very clean and the outdoor space was perfect too. The pool was such a great addition to this house, my 4yo son has been asking to go back to the “pool house” since we left. We’re already checking schedules to see when we can come back for another visit. The location is great too- very close to siesta key beach, the village and all of the local amenities that Sarasota has to offer. I cannot rave about this property enough. I can’t wait to come back for another visit!

Resort Style Beach House w/ Heated Pool & Spa
We loved this Airbnb. Everything was so clean and setup so well. We loved the homey feel as soon as we walked in. The house was well stocked and all amenities worked extremely well. We loved the push button operation of the pool and spa. TVs everywhere! That made it easy to enjoy our favorite sports from anywhere in or outside the house. The host was very responsive and definitely put a lot of thought into what makes sense for family vacations. We built a lot of great memories. Thank you!!
Apartment rentals with a pool

Gateway to Siesta Key - 1/2 Mile to the Beach
Excellent place, unbeatable location, very cozy and comfortable. Chris let us know we could check in early without even asking. I would gladly come back!

Sea Shell Ocean view On Beach Walk everywhere Pool
Amy was the most responsive host I have ever had on Airbnb. I appreciated her hospitality.

On the Beach; Siesta Key SunBum Studio
My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!

Crystal House on Siesta Key Beach
Our stay with Eric was amazing! We needed a quick beach weekend and this exceeded our expectations. His unit was as described with luxury towels and bed linens. Beach closet was bonus…the cart, cooler and chairs was much needed and appreciated! I messaged Eric prior to our arrival asking if there was a volleyball in the closet so I could add to our grocery order if not. First thing I saw as we walked in the unit was a new volleyball sitting on the table awaiting our arrival! Way above and beyond! Easy check in and check out. Actually, our flight was ahead of schedule and Eric allowed us early entry to get our trip started a bit sooner! This was our first time visiting the area and definitely plan on returning and will stay here again. Thanks for a great stay!

Siesta Key Ground Floor Condo 2BR On Trolley Line
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!

The Seabreeze Cottage with peaceful water views
Dear Angela, Thank you so much for hosting us! We absolutely love your decor every detail was so thoughtfully done and made the space feel cozy and "beachy". We truly enjoyed our stay and appreciated how comfortable and well-kept everything was. Hope to visit again someday. All the best. Jianfeng & Yangqing

Siesta Key Beach Front Condo
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!

Shorewalk full condo IMG Beaches Anna Maria
This was a great place and had everything you needed! My family really enjoyed it and the host was amazing to work with and responded back really fast! I would go back here!! Also the beach, omg it’s beautiful!! White sandy beaches, beautiful blue water, we even found whole sand dollars!! Worth checking out and staying!!!
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!

New! Poolside Sunset Serenity In South Gulf Cove

Comfy Home W/ Heated Pool Near Siesta Key Beach
Quick stats about holiday rentals with a pool in Sarasota
Total rentals
870 properties
Nightly prices starting at
$13 SGD before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
680 properties are a good fit for families
Pet-friendly rentals
340 properties allow pets
Rentals with dedicated workspaces
510 properties have a dedicated workspace
Destinations to explore
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Rentals with lake access Sarasota
- Villa rentals Sarasota
- Rentals with a kayak Sarasota
- Fitness-friendly rentals Sarasota
- Rentals with a hot tub Sarasota
- Waterfront rentals Sarasota
- Townhouse rentals Sarasota
- Rentals with a firepit Sarasota
- Beach house rentals Sarasota
- Rentals with outdoor seating Sarasota
- Tiny house rentals Sarasota
- Rentals with a fireplace Sarasota
- Rentals with a patio Sarasota
- Beachfront rentals Sarasota
- Pet-friendly rentals Sarasota
- Family-friendly rentals Sarasota
- Boutique hotel rentals Sarasota
- Rentals with beach access Sarasota
- Flat rentals Sarasota
- Family-friendly rentals Sarasota
- House rentals Sarasota
- Apartment rentals Sarasota
- Rentals with a washing machine and dryer Sarasota
- Beach apartment rentals Sarasota
- Guest house rentals Sarasota
- Private suite rentals Sarasota
- Rentals with breakfast Sarasota
- Rentals with an EV charger Sarasota
- Cottage rentals Sarasota
- Luxury rentals Sarasota
- Smoking-friendly rentals Sarasota
- Bungalow rentals Sarasota
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Things to do Sarasota
- Things to do Sarasota County
- Things to do Florida
- Tours Florida
- Art and culture Florida
- Entertainment Florida
- Wellness Florida
- Food and drink Florida
- Sports activities Florida
- Sightseeing Florida
- Nature and outdoors Florida
- Things to do United States
- Sightseeing United States
- Art and culture United States
- Tours United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Wellness United States
- Entertainment United States