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

Osprey Hotels with Swimming Pool

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Check availability on Osprey Hotels with Swimming Pools

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

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 modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.

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.
RM370
RM468 total
includes taxes & fees
15 Sept - 16 Sept
Casey Key Resorts - Mainland
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A modern bathroom with a shower, a sink, and a mirror.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A modern hotel room with a desk, office chair, sofa, TV, and dining area.

2. Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG
Sarasota
  • Dive into refreshing bliss at this beachside haven with a sparkling outdoor pool and hot tub sanctuary.
RM341
RM386 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express Sarasota East - I-75 by IHG
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.
A hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.

3. 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.
RM378
RM427 total
includes taxes & fees
15 Sept - 16 Sept
Spark by Hilton Sarasota Siesta Key Gateway
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 room with two beds, a nightstand, and a desk.
A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

4. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
RM375
RM424 total
includes taxes & fees
20 Sept - 21 Sept
Comfort Suites Sarasota - Siesta Key
A swimming pool with lounge chairs and palm trees, surrounded by string lights.
A bedroom with a bed, bedside tables, a desk, and a chair.
A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.
A covered outdoor area with a pool, lounge chairs, and a wooden deck.

5. Siesta Key Palms Resort

Siesta Key Palms Resort
Sarasota
  • Dive into paradise with two sparkling outdoor pools surrounded by lush gardens, just a short walk from Crescent Beach.
RM212
RM446 total
includes taxes & fees
16 Sept - 17 Sept
Siesta Key Palms Resort
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A round table with two green placemats, a yellow napkin, and a glass vase with a pink flower.
A pathway leading to a white staircase surrounded by lush greenery and palm trees.
A hotel with a palm tree entrance, a neon sign, and a tiled roof.

6. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
RM391
RM548 total
includes taxes & fees
22 Sept - 23 Sept
Inn at the Beach
A pool area with a waterfall feature, lounge chairs, and palm trees.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.
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.

7. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
RM549
RM726 total
includes taxes & fees
10 Sept - 11 Sept
Tropical Beach Resorts
A swimming pool with a brick border, surrounded by lounge chairs and a fence.
A spacious lobby with a reception desk, seating area, and large windows.
A hotel room with two beds, a nightstand, a lamp, and a large painting of a pier and sunset.
A room with two black leather chairs, a round table, and a lamp.

8. Days Inn by Wyndham Sarasota I-75

Days Inn by Wyndham Sarasota I-75
Sarasota
  • Splash into Florida sunshine at this Sarasota hotel with a serene poolside escape just minutes from Siesta Key Beach.
RM251
RM284 total
includes taxes & fees
10 Sept - 11 Sept
Days Inn by Wyndham Sarasota I-75
A beach with white lounge chairs and striped umbrellas.
A bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.
A modern house with a patio, outdoor seating, and a view of the ocean.
A kitchen with a built-in microwave, a small refrigerator, and a wooden shelf with a coffee maker and other items.

9. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
RM460
RM582 total
includes taxes & fees
23 Sept - 24 Sept
Casey Key Resorts - Beachfront
A swimming pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and palm trees.
A modern kitchen with a stainless steel refrigerator, a built-in microwave, a dishwasher, and wooden cabinetry.
A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

10. 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 cosy loungers.
RM530
RM598 total
includes taxes & fees
6 Oct - 7 Oct
Home2 Suites by Hilton Nokomis Sarasota Casey Key
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Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
5 stars
Beach

Top Osprey Hotel Reviews

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"El servicio de transporte a la playa es muy conveniente."
MARCO 2-night trip
Posted 4 hours ago
The Westin Sarasota
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"This was a quaint little place. I loved it. The pool was nice. It wasn’t far from the beach about 5 miles. The rooms are very clean and the way the property looked was nice and clean and I liked Hall. He decorated it with the tiki hut."
Lenore Us 3-night trip
Posted 7 hours ago
Golden Host Resort - Sarasota
Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Had a lovely stay. I loved that they had fresh coffee in the lobby all day long!"
Susannah 2-night trip
Posted 7 hours ago
Hyatt Place Sarasota/Bradenton Airport
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Great location!!!"
Julissa 3-night trip
Posted 11 hours ago
Tropical Breeze Resort
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Clean and friendly"
Siaosi 2-night trip
Posted 16 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport
Zota Beach Resort

Zota Beach Resort

8/10 Good
"Wonderful beach. Enjoy having free coffee in lobby. The shuttle to St. Armands was great. Nice gym. Disappointed that there are no vegan options in restaurant. Our shower was gross. Not what I expect from Opal."
Beverly 2-night trip
Posted 2 days ago
Zota Beach 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 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. The St. Regis Longboat Key Resort: Hotel located near Mote Marine Laboratory & Aquarium. Offers a private beach, an outdoor pool and a lazy river.
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 Jim Neville Marine Preserve. 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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