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

Hotels with Swimming Pool in Osprey, Florida

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Check availability on Osprey Hotels with Swimming Pool

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.
A balcony with two black chairs, a white railing, and a view of palm trees and a building in the background.
A modern bedroom with a bed, a desk, and a sofa.
A pathway flanked by palm trees and a building with a covered patio area.

1. Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
Osprey
  • Splash into sunshine at this Nokomis retreat featuring a heated pool and tiki bar with live music.
P3,980
P5,038 total
includes taxes & fees
Nov 2 - Nov 3
Casey Key Resorts - Mainland
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.
A spacious living area with a large window overlooking a body of water, a balcony with a view, a kitchen with a TV, and a seating area with a sofa and chairs.
A sandy beach path with wooden posts and ropes, leading towards the ocean.
A wooden deck with chairs and a table overlooking a body of water.

2. Turtle Beach Resort

Turtle Beach Resort
Siesta Key
  • Private hot tubs and a serene outdoor pool await on this peaceful retreat near Turtle Beach.
P12,750
P16,231 total
includes taxes & fees
Nov 1 - Nov 2
Turtle Beach Resort
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.
A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.
An outdoor patio with a fire feature, seating, and a bar area.

3. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
  • Splash into vacation mode with a sparkling poolside sanctuary just steps from Siesta Key Beach.
P5,981
P6,758 total
includes taxes & fees
Oct 12 - Oct 13
Spark by Hilton Sarasota Siesta Key Gateway
A pool area with a waterfall feature, lounge chairs, and palm trees.
A covered patio with a brick floor, wicker furniture, and tropical plants.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.

4. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
P7,991
P10,662 total
includes taxes & fees
Oct 11 - Oct 12
Tropical Beach Resorts
A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
A reception area with two reception desks, a blue geometric wall design, and a wooden panel accent.
A conference room with a long table, blue chairs, framed artwork on the walls, and a Holiday Inn Express sign.
A modern bathroom with a geometric tile pattern, a large mirror, a white sink, and a glass-enclosed shower.

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

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.
P6,345
P7,170 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
A rectangular pool with a tiled edge, surrounded by a brick patio. There are lounge chairs and umbrellas, and a fence enclosing the area.
A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.
A hotel room with two beds, a nightstand, and a desk.
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

6. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
P6,354
P7,180 total
includes taxes & fees
Oct 18 - Oct 19
Comfort Suites Sarasota - Siesta Key
A swimming pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and palm trees.
Bathroom
A hotel room with a sofa, a desk, a lamp, a television, and a window with patterned curtains.
A compact kitchen with a microwave, sink, and dishwasher.

7. Home2 Suites by Hilton Nokomis Sarasota Casey Key

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.
P8,233
P9,303 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Nokomis Sarasota Casey Key
A swimming pool area with a tiled deck, lounge chairs, and a covered seating area.
A spacious living area with a wooden floor, teal upholstered furniture, and a central coffee table.
A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a TV.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, and a view of the outdoors.

8. Hampton Inn & Suites Venice Bayside South Sarasota

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.
P7,956
P8,991 total
includes taxes & fees
Oct 16 - Oct 17
Hampton Inn & Suites Venice Bayside South Sarasota
A hotel pool area with lounge chairs and a covered seating area.
A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.
A hotel room with two beds, a kitchenette, a TV, and a desk.
A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.

9. Carlisle Inn

Carlisle Inn
Pinecraft
  • Refresh yourself poolside under the Florida sun in this tranquil Pinecraft sanctuary.
P8,996
P10,165 total
includes taxes & fees
Oct 11 - Oct 12
Carlisle Inn
A rooftop pool area with lounge chairs and umbrellas, overlooking a cityscape during sunset.
A modern lobby with a vertical garden, comfortable seating, and a geometric light fixture.
A modern hotel room with a large balcony, a dining area, and a view of the cityscape.
A rooftop bar with seating and a bar area, overlooking a cityscape at dusk.

10. The Westin Sarasota

The Westin Sarasota
Central Sarasota
  • Take a plunge into heated pool magic at this Westin with rooftop terrace in Sarasota.
P16,271
P19,948 total
includes taxes & fees
Nov 2 - Nov 3
The Westin Sarasota
View all properties

Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
5 stars
Beach

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"I’m"
jessica 2-night trip
Posted 13 hours ago
Spark by Hilton Sarasota Siesta Key Gateway
Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"Great place- wonderful staff"
Debra 6-night trip
Posted 16 hours ago
Lido Beach Resort
Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Excellent upscale hotel on the beach. Everyone here was very accommodating."
Gary 2-night trip
Posted 17 hours ago
Zota Beach Resort
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Front desk was very friendly!"
Michael 1-night trip
Posted 2 days ago
Casey Key Resorts - Mainland
Tropical Breeze Resort

Tropical Breeze Resort

8/10 Good
"Great location, close to restaurants and shops."
Frank 2-night trip
Posted 3 days ago
Tropical Breeze Resort

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.

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