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

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Check availability on Osprey Hotels with a Pool

Tonight
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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 restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.
A modern bedroom with a bed, a desk, and a sofa.

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.
NT$2,874
NT$3,637 total
includes taxes & fees
Sep 12 - Sep 13
Casey Key Resorts - Mainland
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 hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

2. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
NT$2,924
NT$3,305 total
includes taxes & fees
Sep 27 - Sep 28
Comfort Suites Sarasota - Siesta Key
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.
An outdoor patio with a fire feature, seating, and a bar area.
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.
A hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.

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.
NT$2,941
NT$3,324 total
includes taxes & fees
Sep 13 - Sep 14
Spark by Hilton Sarasota Siesta Key Gateway
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A modern bathroom with a shower, a sink, and a mirror.
A modern hotel room with a desk, office chair, sofa, TV, and dining area.

4. 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.
NT$2,745
NT$3,102 total
includes taxes & fees
Sep 16 - Sep 17
Holiday Inn Express Sarasota East - I-75 by IHG
A swimming pool with lounge chairs and palm trees, surrounded by string lights.
A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.
A bedroom with a bed, bedside tables, a desk, and a chair.
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.
NT$1,648
NT$3,466 total
includes taxes & fees
Sep 17 - Sep 18
Siesta Key Palms Resort
A rectangular swimming pool with white lounge chairs on both sides, surrounded by palm trees and a wooden fence.
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.
An aerial view of a coastal area with a sandy beach, a row of houses, and a clear sky.

6. 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.
NT$2,577
NT$4,868 total
includes taxes & fees
Sep 13 - Sep 14
Escape Coastal Resort on Casey Key
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.
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.

7. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
NT$3,044
NT$4,258 total
includes taxes & fees
Sep 22 - Sep 23
Inn at the Beach
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 Days Inn with a yellow facade, arched entrance, and a well-maintained garden with palm trees and shrubs.
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.
NT$1,902
NT$2,150 total
includes taxes & fees
Sep 13 - Sep 14
Days Inn by Wyndham Sarasota I-75
A swimming pool area with a tiled deck, lounge chairs, and a covered seating area.
A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a TV.
A spacious living area with a wooden floor, teal upholstered furniture, and a central coffee table.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, and a view of the outdoors.

9. 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.
NT$3,586
NT$4,053 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn & Suites Venice Bayside South Sarasota
A pool area with lounge chairs and umbrellas, surrounded by a fence and palm trees.
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.
A hotel room with two beds, a sofa, a desk, a TV, and a painting on the wall.
A hotel lobby with two brown sofas, a red sofa with gold patterns, a coffee station, and a reception desk.

10. Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice
Venice
  • Dive into poolside perfection with loungers and umbrellas at this Venice retreat.
NT$2,772
NT$3,133 total
includes taxes & fees
Sep 13 - Sep 14
Best Western Plus Ambassador Suites Venice
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

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"The staff was very helpful and attentive."
Jose 2-night trip
Posted 9 hours ago
Siesta Key Beach Resort and Suites
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"With in walking of everything. Easy going place. Excellent coffee, relaxing pool."
Dawn 2-night trip
Posted 12 hours ago
Tropical Breeze Resort
Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Q no lo duden q es un lugar espectacular y muy acogedor"
Yeisy 3-night trip
Posted 18 hours ago
Tropical Beach Resorts
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"My room was spacious clean and comfortable. My husband said it was wonderful."
Marc 1-night trip
Posted 2 days ago
DoubleTree by Hilton Sarasota Bradenton Airport

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: Hotel, 12-minute walk from John and Mable Ringling Museum of Art. 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. 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 like Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions like 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 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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