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

Hotels with Swimming Pools in Osprey

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Check availability on Osprey Hotels with Swimming Pools

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.
A modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.
A balcony with two black chairs, a white railing, and a view of palm trees and a building in the background.
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.
S$137
includes taxes & fees
5 Oct - 6 Oct
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 wooden deck with chairs and a table overlooking a body of water.
A narrow stone pathway flanked by lush green plants and a wooden pergola structure.
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.

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.
S$324
includes taxes & fees
1 Nov - 2 Nov
Turtle Beach Resort
A pool area with a waterfall feature, lounge chairs, and palm trees.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
A covered patio with a brick floor, wicker furniture, and tropical plants.
A beach with white sand, clear blue water, and a few beach umbrellas.

3. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
S$228
includes taxes & fees
4 Oct - 5 Oct
Tropical Beach Resorts
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.
An outdoor patio with a fire feature, seating, and a bar area.
A hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.

4. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
  • Splash into holiday mode with a sparkling poolside sanctuary just steps from Siesta Key Beach.
S$147
includes taxes & fees
5 Oct - 6 Oct
Spark by Hilton Sarasota Siesta Key Gateway
A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
A modern bathroom with a geometric tile pattern, a large mirror, a white sink, and a glass-enclosed shower.
A modern lobby with a sofa, chairs, a desk, and a map mural on the wall.
A conference room with a long table, blue chairs, framed artwork on the walls, and a Holiday Inn Express sign.

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.
S$152
includes taxes & fees
14 Oct - 15 Oct
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 lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.
A hotel room with two beds, a nightstand, and a desk.
A hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

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.
S$137
includes taxes & fees
29 Oct - 30 Oct
Comfort Suites Sarasota - Siesta Key
A rectangular swimming pool with white lounge chairs on both sides, surrounded by palm trees and a wooden fence.
A marina with boats docked, surrounded by residential buildings and palm trees.
A modern living room with a grey sofa, a blue patterned armchair, a dining area with wicker chairs, and a view through glass doors to an outdoor patio.
A living room with a TV, white cabinets, a sofa, and a balcony with a view.

7. Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key
Casey Key
  • Coastal retreat features serene waters and a sun-soaked outdoor pool with loungers and umbrellas.
S$198
includes taxes & fees
5 Oct - 6 Oct
Escape Coastal Resort on Casey Key
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a multi-story building.
Beach
A modern bathroom with a glass shower enclosure, a double sink vanity, and a large mirror.
A bedroom with a bed, a TV, a wooden dresser, and a bathroom visible through an open door.

8. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
South Village
S$170
includes taxes & fees
4 Oct - 5 Oct
Cottages at Siesta Key Inn
A rectangular swimming pool with a clear blue waterline, surrounded by a brick patio with outdoor seating.
A narrow concrete pathway flanked by lush tropical plants, leading to a wooden gate.
A beach with white sand, wooden beach chairs, and a clear blue sky.
A dining table with glassware and decorative branches, set outdoors with a house in the background.

9. Captiva Beach Resort

Captiva Beach Resort
South Village
  • Splash into beachside serenity with a pristine pool just steps from Siesta Key's famous white sand shores.
S$247
includes taxes & fees
6 Oct - 7 Oct
Captiva Beach Resort
A beach with white lounge chairs and striped umbrellas.
A modern house with a patio, outdoor seating, and a view of the ocean.
A bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.
A kitchen with a built-in microwave, a small refrigerator, and a wooden shelf with a coffee maker and other items.

10. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
S$184
includes taxes & fees
1 Nov - 2 Nov
Casey Key Resorts - Beachfront
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

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"The resort was close to the beach and restaurants. Definitely a great place to stay, the rooms were very clean and the staff were courteous and very helpful."
Milton 2-night trip
Posted 1 hour ago
Tropical Breeze Resort
The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Clean, comfortable and quiet rooms. Excellent location with lots of great restaurants nearby. The hotel staff are friendly and welcoming. We had an enjoyable weekend stay with family. The rooftop pool is lovely."
Kathrine 3-night trip
Posted 3 hours ago
The Westin Sarasota
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Our stay was great—the room was clean, and there was free transportation to the beach. Everything was very good."
Alecssandre 2-night trip
Posted 22 hours ago
Casey Key Resorts - Mainland
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Esta bonito y a pasos de la playa"
Mabel 1-night trip
Posted 1 day ago
Siesta Key Beach Resort and Suites
Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"La limpieza lo acogedor y la tranquilidad que habia, las piscinas limpias me agrado mucho seguro volvere a repetir."
Ranses 3-night trip
Posted 1 day ago
Tropical Beach Resorts

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 high-speed (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 swimming 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 such as Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions such as 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 the local weather in Osprey into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 19°C. Average annual precipitation for Osprey is 1126 mm.

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