The Best Hotels with a Pool in Osprey, FL from ￥13,699 in 2026

Q: What are some hotels with pools in Osprey?

Casey Key Resorts - Mainland : Features a snack bar/deli, an outdoor pool, and complimentary wired internet access. Kompose Boutique Hotel : Offers a snack bar/deli, a pool, and complimentary wireless internet access. Tropical Beach Resorts : Aparthotel, 10-minute walk from Crescent Beach. Provides free self parking, 2 outdoor pools, and complimentary wireless internet access. The Westin Sarasota : Hotel located near Lido Beach. Features 2 restaurants, an outdoor pool, and a full-service spa. Siesta Key Beach Resort and Suites : Resort, 1-minute walk from Siesta Key Beach. Offers complimentary bicycles, a pool, and complimentary wireless internet access.

A marina with docked boats, a wooden bridge, and a building with a red roof.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Osprey Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.

1. Casey Key Resorts - Mainland

Osprey

Splash into sunshine at this Nokomis retreat featuring a heated pool and tiki bar with live music.

￥13,699 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with a 3 ft 3 in depth marker, surrounded by lounge chairs and a covered seating area with a view of the water.

2. Turtle Beach Resort

Siesta Key

Private hot tubs and a serene outdoor pool await on this peaceful retreat near Turtle Beach.

￥39,534 total

includes taxes & fees

Nov 23 - Nov 24

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.

3. Spark by Hilton Sarasota Siesta Key Gateway

Sarasota

Splash into vacation mode with a sparkling poolside sanctuary just steps from Siesta Key Beach.

￥19,735 total

includes taxes & fees

Nov 11 - Nov 12

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.

4. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Nokomis

Escape to a refreshing pool retreat near Venice Beach where outdoor relaxation meets coastal adventure.

￥18,007 total

includes taxes & fees

Nov 2 - Nov 3

A rectangular pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and umbrellas, and a fence enclosing the area.

5. Comfort Suites Sarasota - Siesta Key

Sarasota

Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.

￥17,671 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and palm trees.

6. Home2 Suites by Hilton Nokomis Sarasota Casey Key

Nokomis

Dive into aquatic bliss at this Sarasota gem with a sun-drenched pool and cozy loungers.

￥21,049 total

includes taxes & fees

Nov 16 - Nov 17

A pool area with a waterfall feature, lounge chairs, and palm trees.

7. Tropical Beach Resorts

South Village

Sparkling private beachfront pool awaits just steps from your villa-style retreat.

￥28,848 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool area with a tiled deck, lounge chairs, and a covered seating area.

8. Hampton Inn & Suites Venice Bayside South Sarasota

Gateway

Sun-drenched relaxation awaits at this Venice hotel's outdoor pool, complemented by beach proximity and modern comforts.

￥19,396 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Choose what matters most at hotels with a pool in Osprey

Breakfast included

Hot tub

Top Osprey Hotel Reviews

Cirque St. Armands Beachside

10/10 Excellent

"Best time ever. A new hotel with a great vibe, attention to detail & a welcoming, engaging professional staff. Front desk check in was quick and very informative..with a complimentary signature Prosecco to start the evening. The restaurant on site, Ringside, is 5 Stars .. excellent food, relaxing ambiance and our server Danilo was attentive and made it a delightful dinner experience. Highly recommend. Everything was Exceptional!"

Tropical Beach Resorts

10/10 Excellent

"The grounds were well kept, check-in was an ease on the staff was very pleasant and professional. Our room was very clean well equipped with everything we needed. Super quick walk to the beach in the pool area was really nice. Great location of any options for public transportation, which may getting around and ease without the need to rent a vehicle. We would definitely stay here again."

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good

"If I had known hot tub was not working, I would have not booked or stayed there. Chose this property because after a very long driving day, i just needed that soak! Speaking of soaking.... there are ZERO directions how to turn water on your goofy showers...so no water for me this stay, at all!"

Casey Key Resorts - Mainland

10/10 Excellent

"I received excellent customer service at Casey Key Resorts. They truly care about their guests. When I checked in, I was greeted by Nan. She was very accommodating to my room request. The next day, I had another request and spoke with Nicole at the front desk. She provided me with exceptional customer service to ensure that I had a very comfortable and peaceful staycation. Thank you!😊💜"

Frequently asked questions

What are some hotels with pools in Osprey?

Casey Key Resorts - Mainland: Features a snack bar/deli, an outdoor pool, and complimentary wired internet access. Kompose Boutique Hotel: Offers a snack bar/deli, a pool, and complimentary wireless internet access. Tropical Beach Resorts: Aparthotel, 10-minute walk from Crescent Beach. Provides free self parking, 2 outdoor pools, and complimentary wireless internet access. The Westin Sarasota: Hotel located near Lido Beach. Features 2 restaurants, an outdoor pool, and a full-service spa. Siesta Key Beach Resort and Suites: Resort, 1-minute walk from Siesta Key Beach. Offers complimentary bicycles, a pool, and complimentary wireless internet access.

What is there to see and do in Osprey?

Explore places like Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions like Turtle Beach and Nokomis Beach. Osprey appeals to visitors with its beautiful beaches, bar scene, and array of dining options.

When is the best time to book a hotel with a pool in Osprey?

Taking into account the local weather in Osprey can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Osprey is 44 inches.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Osprey on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Osprey Hotels with a Pool