Vacation rentals with a pool in Osprey

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Popular amenities for Osprey rentals with a pool

House rentals with a pool

Guest favorite

Home in North Port

5 out of 5 average rating, 12 reviews

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

JenniferRating, 5 stars3 weeks ago
Great Place to stay. If ever in the area would stay again.
Guest favorite

Home in Rotonda West

4.94 out of 5 average rating, 68 reviews

Luxury Pool & Spa Villa with 2 Master Suites

SandraRating, 5 stars4 months ago
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.
Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 76 reviews

Serenity 4BR HOME Amazing Heated Pool and Spa!

RhiannonRating, 5 stars2 weeks ago
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!
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 stars1 month ago
Great stay. This place is near to beaches in Sarasota. Host is very responsive .
Guest favorite

Home in Siesta Key

5 out of 5 average rating, 27 reviews

Beautiful House with Heated pool

SarahRating, 5 stars4 months ago
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!
Superhost

Home in North Port

4.86 out of 5 average rating, 36 reviews

Tropical Pool Vacation Getaway!

JeffRating, 5 stars1 week ago
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.
Guest favorite

Home in North Port

4.94 out of 5 average rating, 35 reviews

Entire Home. 2/bd & 2/bath with Pool.

ElizabethRating, 5 stars6 days ago
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.
Guest favorite

Home in Sarasota

4.92 out of 5 average rating, 25 reviews

Beautiful, Spacious Heated Pool Home

EricRating, 5 stars3 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, 9 reviews

Tropical Haven *A

CarrieRating, 5 stars2 months ago
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
Guest favorite

Condo in Bradenton

5 out of 5 average rating, 5 reviews

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

AnnaBelleRating, 5 stars1 month ago
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.
Superhost

Condo in Englewood

4.87 out of 5 average rating, 45 reviews

Condo With Heated Pool, Beaches Only Minutes Away

KarenRating, 5 stars7 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 stars11 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 stars5 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, 70 reviews

Lakeside Condo. Beaches, Restaurants, IMG nearby.

KarinaRating, 5 stars1 month 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 stars1 month 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 stars5 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.

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

Destinations to explore

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