Vacation rentals with a pool in Osprey

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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 stars7 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!
Guest favorite
Home in North Port
5 out of 5 average rating, 13 reviews

3bd 2th Solar Heat Pool Large home W/ big yard

Lee And LeslieRating, 5 stars1 month ago
Bigger than it looks in the pictures! Very very clean! Great stay!
Superhost
Home in Sarasota
4.93 out of 5 average rating, 135 reviews

Centrally located oasis.

JacobRating, 5 stars7 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.
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 77 reviews

Spacious 4BR Getaway – Perfect for Families!

JoelRating, 5 stars2 weeks ago
We stay at a lot of Airbnb's and found this one to be particularly easy and satisfying. The place was exactly as described in the listing. One nice thing is it was better-stocked than many, with things like coffee, basic seasonings and other non-perishable items were there. Lots of extra towels/pillows/blankets, shower soap, dishwasher soap, washing machine soap - stuff like that was all ready to go.
Superhost
Home in Bradenton
4.87 out of 5 average rating, 289 reviews

Large 4 bedroom pool home tiki bar close to Ami

RaghuRating, 5 stars2 months ago
Great stay. This place is near to beaches in Sarasota. Host is very responsive .
Superhost
Home in North Port
4.85 out of 5 average rating, 39 reviews

Tropical Pool Vacation Getaway!

BradleyRating, 5 stars3 days ago
We absolutely loved the home. It was super clean and just as advertised. Our little boy loved the heated pool. It was perfect. The neighborhood is quiet and convenient to lots of restaurants. Beds are comfortable. I would not hesitate to stay here again.
Guest favorite
Home in Sarasota
4.92 out of 5 average rating, 25 reviews

Beautiful, Spacious Heated Pool Home

EricRating, 5 stars4 months ago
Very comfortable stay would definitely stay again.

Condo rentals with a pool

Guest favorite
Condo in Bradenton
5 out of 5 average rating, 7 reviews

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

JimRating, 5 stars4 days ago
Host was fast to reply. Place was lovely. Convenient to all the activities we planned (baseball spring training, golf, beach and restaurants). Only issue was bedroom drawer was off track and host was notified and appreciated we let her know and will address. The jacuzzi jets were not working, but I wouldn’t hold that against the host. I would stay her again.
Superhost
Condo in Englewood
4.87 out of 5 average rating, 45 reviews

Condo With Heated Pool, Beaches Only Minutes Away

KarenRating, 5 stars8 months ago
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 !
Superhost
Condo in Osprey
4.89 out of 5 average rating, 9 reviews

Lovely 2 bedroom condo with pool & tennis courts

MarlynRating, 5 stars12 months ago
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.
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 stars6 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.
Superhost
Condo in Bradenton
4.87 out of 5 average rating, 71 reviews

Lakeside Condo. Beaches, Restaurants, IMG nearby.

KarinaRating, 5 stars2 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 stars2 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.
Guest favorite
Condo in Bradenton Beach
4.86 out of 5 average rating, 103 reviews

Oceanfront Condo for Beach Lovers

DonaldRating, 5 stars6 months ago
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.
Guest favorite
Condo in Siesta Key
4.94 out of 5 average rating, 100 reviews

Siesta Key Beach Front Condo

AnneRating, 5 stars2 weeks ago
We loved our stay! Ideal location across from siesta key beach and one mile walk or free trolley ride into town with lots of restaurants, shops and a gourmet supermarket. The condo was clean, comfortable and well stocked and Evan was very responsive to any questions we had.

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