Vacation rentals with a pool in Osprey
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Osprey
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Osprey rentals with a pool
House rentals with a pool
Home in North Port
5 out of 5 average rating, 12 reviews3bd 2th Solar Heat Pool Large home W/ big yard
Great Place to stay. If ever in the area would stay again.
Home in Rotonda West
4.94 out of 5 average rating, 68 reviewsLuxury Pool & Spa Villa with 2 Master Suites
Another wonderful stay at Diane’s villa.Everything anybody can want on a vacation ,lovely villa ,very peaceful location,driving distance to beaches and large choice of restaurants.We had our flight home to UK cancelled due to hurricane Helene but Diane checked in on us all the time and allowed us to rearrange our departure which was such a relief.Not an experience we wish to repeat but look forward to a return visit next spring.
Home in Sarasota
4.97 out of 5 average rating, 76 reviewsSerenity 4BR HOME Amazing Heated Pool and Spa!
Our stay at Max's place was smooth and carefree! We were able to check in early and without any complications. The home was just as described. I would highly recommend staying here!
Home in Bradenton
4.87 out of 5 average rating, 289 reviewsLarge 4 bedroom pool home tiki bar close to Ami
Great stay. This place is near to beaches in Sarasota. Host is very responsive .
Home in Siesta Key
5 out of 5 average rating, 27 reviewsBeautiful House with Heated pool
Our girls trip weekend was a huge success!! We all had a wonderful stay here and we didn’t have a single complaint. Check in was super easy and went off without a hitch. The house is exactly as pictured, very open and comfortable. We did not have a single issue while staying! Highly recommend staying here, I promise we will be back!
Home in North Port
4.86 out of 5 average rating, 36 reviewsTropical Pool Vacation Getaway!
My family came from Germany and Texas for a family vacation. We had an amazing time and loved the heated pool. The house work wonderful for us.
Home in North Port
4.94 out of 5 average rating, 35 reviewsEntire Home. 2/bd & 2/bath with Pool.
Wonderful place. It was easy to find, in a great neighborhood, and extremely clean upon check-in. Deanna was very responsive to questions and gave us lots of suggestions on where to eat, shop, etc. It’s in a great neighborhood with lots of choices. It’s also close to other areas like Port Charlotte, Punta Gorda, Englewood, and Venice. Everything seems to be within a short drive. Visited several beaches and it was extremely helpful to have a full-size washer and dryer. We will definitely return.
Home in Sarasota
4.92 out of 5 average rating, 25 reviewsBeautiful, Spacious Heated Pool Home
Very comfortable stay would definitely stay again.
Condo rentals with a pool
Condo in Bradenton
5 out of 5 average rating, 9 reviewsTropical Haven *A
The host was not responsive during our stay but overall the condo and outside amenities ie pool and yard were well taken care of and had all the extras that were needed to make the stay very enjoyable. The streets were still being cleaned up from the hurricanes but this property has been cleaned inside and out and is very relaxing oasis
Condo in Bradenton
5 out of 5 average rating, 5 reviewsLovely Condo, Heated Pools, AMI, IMG, Top beaches
This condo was nice for a central location. We went to downtown Bradenton to the Bishop Museum, to Anna Maria Island and to Palmetto. The kitchen had all the basics and the freezer has an ice machine which was nice. We utilized the beach towels only but they also provide beach chairs and some pool noodles. There was some siren noise from the main streets near by, but nothing awful. Lots of closet space, great to have a washer and dryer and the guest bath has been nicely redone. We would stay here again.
Condo in Englewood
4.87 out of 5 average rating, 45 reviewsCondo With Heated Pool, Beaches Only Minutes Away
I thoroughly enjoyed the ARBNB . It was very clean and I felt like I was right at home . The kitchen was well stocked and the appliances worked perfectly . I loved the washer and dryer! It was close to restaurants and beaches . The location was quiet and close to beaches . Would highly recommend property to anyone traveling. Plus the pool was clean and close to unit !
Condo in Osprey
4.89 out of 5 average rating, 9 reviewsLovely 2 bedroom condo with pool & tennis courts
This is our second year staying in this complex. There are many walking trails that are a short drive, close to several beaches, restaurants and grocery stores.
Condo in Siesta Key
4.87 out of 5 average rating, 101 reviewsSiesta Village Short Walk to Beach w heated Pool
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.
Condo in Bradenton
4.87 out of 5 average rating, 70 reviewsLakeside Condo. Beaches, Restaurants, IMG nearby.
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 !
Condo in Sarasota
4.97 out of 5 average rating, 61 reviewsPeaceful retreat, pool, hot tub, near Siesta Key!
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.
Condo in Bradenton Beach
4.86 out of 5 average rating, 103 reviewsOceanfront Condo for Beach Lovers
Ulrike's apartment was perfect for two couples. It was very clean and well maintained. The high quality furnishings were comfortable and met out needs. The view was outstanding! Parking under the first floor was a big plus, with an elevator to our floor. We felt safe and had privacy.
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
280 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
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