Vacation rentals with a pool in Osprey

Find and book unique homes with a pool on Airbnb

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Popular amenities for Osprey rentals with a pool

House rentals with a pool

Superhost
Home in Sarasota
4.63 out of 5 average rating, 19 reviews

Vitamin Sea: Private Pool, Downtown, and Beaches!

LindaRating, 5 stars9 months ago
My family and I stayed here for 10 days and we can say it was one of the best stays. Our flight landed early and we reached out to the host to ask for an early check in, they responded back fast and were able to accommodate us. Once inside the house everything was clean and the kids went right into the pool which was also very clean. Overall we felt right at home and the whole stay was 10/10!
Superhost
Home in Sarasota
4.93 out of 5 average rating, 135 reviews

Centrally located oasis.

JacobRating, 5 stars9 months ago
The place was mostly what it said it would be, the pictures are accurate. Was pretty nice and cozy. Had lots of privacy, which was really nice. House was clean and had all of the amenities that were promised. Bed was really comfortable. The only drawback was that the pool was a little dirty, looked like it hadn’t been cleaned for a few days before we got there but it wasn’t that big of a deal.
Superhost
Home in Venice
4.56 out of 5 average rating, 16 reviews

Lovely pool house 5 minutes from the beach

LindaRating, 5 stars12 months ago
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.
Superhost
Home in North Port
4.81 out of 5 average rating, 134 reviews

Luxury villa 4 bdr with a heated pool (14guests)

TroyRating, 5 stars2 months ago
Leyla's property was perfect for our stay. Came to visit our grandkids who lived in North Port and gave us a great spot to relax at the end of the night.
Superhost
Home in Bradenton
4.87 out of 5 average rating, 290 reviews

Large 4 bedroom pool home tiki bar close to Ami

JohnRating, 5 stars6 days ago
We were able to book a 3 night stay last minute and the hosts were super easy to work with. The house was more than we needed and everything available to make our stay enjoyable. They were quick to respond and answer questions. House is super clean and location allowed us to get to the beach and away from it when needed. We appreciate the space that allowed us to relax and unwind after a busy week.
Superhost
Home in North Port
4.85 out of 5 average rating, 41 reviews

Tropical Pool Vacation Getaway!

JosephRating, 5 stars1 month ago
Beautiful place to stay. Kitchen was well equipped. Only couple complaints (if you call it that)…my husband and I would have liked to see full beds in the bedroom with twin beds, maybe a few bath and kitchen towels, a dresser in the spare bedrooms sure would have been nice to put clothes in or suitcases on, maybe a tv in each bedroom, the garage door opener didn’t work. Sounds spoiled but just what we are used to. Pool was absolutely amazing!! Gas grill worked just great!
Top guest favorite
Home in North Port
4.82 out of 5 average rating, 11 reviews

Cozy Home with Heated Pool

ChandlerRating, 5 stars1 month ago
This home was perfect for our vacation. It was a quiet neighborhood and close to our planned activities. Everything was like the listing described. Elina was a wonderful host who made sure to reach out to us and answered any questions I had.
Superhost
Home in Venice
4.88 out of 5 average rating, 17 reviews

Private Heated Pool & Spa. Walk to Shamrock Park.

MarcieRating, 5 stars1 month ago
Ryan’s place was just right for our escape from the Wisconsin winter! We walked every morning to the Shamrock park and Nature center. Great restaurants and shopping in Venice.

Condo rentals with a pool

Guest favorite
Condo in Bradenton
5 out of 5 average rating, 10 reviews

Lovely Condo, Heated Pools, AMI, IMG, Top beaches

Luis AlbertoRating, 5 stars6 days ago
Perfect service, very friendly, comfortable and well-located area
Superhost
Condo in Englewood
4.87 out of 5 average rating, 46 reviews

Condo With Heated Pool, Beaches Only Minutes Away

DanRating, 5 stars5 days ago
We were pleasantly surprised by Nicole’s apartment. It was extremely clean, lots of towels, linen, well appointed kitchen and everything else needed to make it like home. We didn’t need to buy or bring anything for the beach because we had beach chairs and an umbrella which were in really great shape. The apartment is within a short driving distance to beaches, stores, restaurants and shop. We had a great time and felt right at home. We highly recommend her place to anyone vacationing in the area.
Superhost
Condo in Holmes Beach
4.83 out of 5 average rating, 6 reviews

1 block from beach + pool - Cayman Cay #102

JoeRating, 5 stars8 months ago
This place was PERFECT! Beautifully decorated to match the beach aesthetic. Literally a one minute walk to the beach! I loved that the place had plenty of towels (both bath and beach), every kitchen utensil and cooking dish you could think of. (We travelled with a teen, a 6 year old and a 10 month old for a week so we cooked a lot.) There was plenty of bedding to use (we enjoyed being able to bring the kids out to the living room and use the pull out sofa for a family movie/game night). There were board games there to use and the biggest plus was the owner was nice enough to allow us to use the accessories he had for the beach at no additional charge. (Beach wagon, chairs, umbrellas, toys, floats). WiFi worked great. AC worked great. Communication was seamless! Told my spouse I couldn’t wait to go back again. Russell and Cindy were incredible to work with. Highly recommend!
Superhost
Condo in Osprey
4.92 out of 5 average rating, 12 reviews

Lovely 2 bedroom condo with pool & tennis courts

CariRating, 5 stars2 weeks ago
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!
Guest favorite
Condo in Siesta Key
4.87 out of 5 average rating, 101 reviews

Siesta Village Short Walk to Beach w heated Pool

CoryRating, 5 stars8 months ago
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.
Guest favorite
Condo in Bradenton
4.84 out of 5 average rating, 126 reviews

Shorewalk upgraded condo upstairs unit 4415

BrianRating, 5 stars2 months ago
Enjoyed our stay. Very quiet location and convenient to everything
Superhost
Condo in Bradenton
4.87 out of 5 average rating, 71 reviews

Lakeside Condo. Beaches, Restaurants, IMG nearby.

KarinaRating, 5 stars3 months ago
This was a great stay !! The location very convenient ! Very nice and place ! Has 2 bathrooms ! Access to the back yard with a nice pond view ! It has balls and games for the family to use ! And chairs to take to the beach ! Will be back ! Totally recommend !
Guest favorite
Condo in Sarasota
4.97 out of 5 average rating, 61 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

JulieRating, 5 stars3 months ago
Great place to stay! It was a very safe community with nice extras and was pretty close to the beaches. So nice to have the extra beach supplies to go shark tooth hunting at Caspersen Beach. The condo was clean and spacious.

Quick stats about vacation rentals with a pool in Osprey

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    290 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey
  6. Rentals with pools