
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
Get the amount of space that is right for you
Popular amenities for Osprey rentals with a pool
House rentals with a pool

Luxury Oasis Home 3BR 2Bath with Heated Pool
Fantastic location if showing at Fox Lea. House was exactly as photographed and very comfortable.

3-bedroom home with pool
Marilyn was very responsive when I needed her, and the place looked exactly like the pictures posted. It’s only 8 minutes driving to Nokomis Beach and same for Downtown Historic Venice where you can find all the good local places to eat and buy gifts, as well as Venice Beach at the end of downtown . Publix is very close if you need to buy groceries. Everything was provided at the house, even things for the beach. The house was beautiful and the location was great and quiet. The pool didn’t disappoint. My grandkid loved it . We all did. I recommend 100% this place! Spacious, clean, beautiful and convenient. If it’s available in the future I will stay here again.

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!

Living The Dream: Heated Pool + Mini Golf +Swings
We really enjoy to stay at the house that is perffect spot to relax is a quiet neighborhood. We'll definitely recommend and came back soon.

The Pineapple Escape
Our family had a wonderful stay at Claudia's home! She is a very friendly and responsive host. The neighborhood is quiet and in a central location to many wonderful beaches and restaurants. The house and pool were very clean and stocked with many kitchen, bathroom and pool essentials. We definitely recommend the Pineapple Escape!!

Siesta Key Modern Retreat with Heated Pool & Spa
The house was tucked into a quiet residential community. The home was clean, fresh and spacious. The guest house area with its own bathroom is perfect for a two family stay! The neighborhood was safe to walk in- I walked daily. The neighborhood was really within 15 minutes drive of anything we wanted to do. We spent most of our time at Siesta Key! Leave EARLY for the beach, if that's your day's plan! We would definitely stay again!

3 bedroom Heated salt water pool close to Siesta
Very beautiful home! Great place to stay and enjoy as well as just close enough to Siesta Keys beach! Peaceful and very clean!! Definitely a must stay!!

Right on the bay! Heated pool! King bed
We had a awesome stay, sergiy was excellent in communication his home is beautiful and very clean. Book this place you will NOT regret. Thanks Sergiy
Condo rentals with a pool

Sea Shell Ocean view On Beach Walk everywhere Pool
Loved the location and the layout of the condominium! We will be coming back!

On the Beach; Siesta Key SunBum Studio
This wasn’t our first time at the Sun Bum … it’s the perfect get away spot. As close to the beach as you can get, has everything you need, and the hosts are BEYOND accommodating. We came for our birthday and they had a birthday banner hung on the wall waiting with a bottle of prosecco. They really make you feel special! If you’re looking for a wonderful spot for you and your spouse, this is the place!!

LIDO KEY 1 BR/1Bath Heated Pool 16
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

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!

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

Condo with a View 1: Open Friday, $250/nt!
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛

Siesta Key Beach Front Condo
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!

Shorewalk full condo IMG Beaches Anna Maria
I've stayed in Shorewalk 4 different times now, but you're place has been the best, by far. Super clean and accommodating. Great communication and always quick to respond. Thank you!
Quick stats about vacation rentals with a pool in Osprey
Total rentals
50 properties
Nightly prices starting at
R1,070 ZAR before taxes and fees
Total number of reviews
390 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Pet-friendly rentals Osprey
- House rentals Osprey
- Fitness-friendly rentals Osprey
- Rentals with a fire pit Osprey
- Rentals with a hot tub Osprey
- Family-friendly rentals Osprey
- Rentals with a patio Osprey
- Rentals with a washer and dryer Osprey
- Rentals with outdoor seating Osprey
- 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
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- North Beach At Fort DeSoto Park
- River Strand Golf and Country Club
- Myakka River State Park
- Alafia River State Park
- North Jetty Beach