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

Osprey Hotel with Pool

  • 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 Hotel with Pool

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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.
HK$667
HK$844 total
includes taxes & fees
5 Oct - 6 Oct
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.
HK$760
HK$859 total
includes taxes & fees
4 Oct - 5 Oct
Comfort Suites Sarasota - Siesta Key
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 hotel room with two beds, a desk, a chair, a TV, and a window with blinds.

3. 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.
HK$620
HK$700 total
includes taxes & fees
25 Sept - 26 Sept
Holiday Inn Express Sarasota East - I-75 by IHG
A swimming pool area with lounge chairs and a building with multiple windows and doors.
A hotel entrance with a red and yellow sign, palm trees, and a parking lot.
A modern hotel room with a kitchenette, a bed, a desk, and a chair.
A breakfast bar with a 'Good Morning' sign, a 'Inspired Table' sign, and various breakfast items and utensils.

4. Home2 Suites Sarasota I-75 Bee Ridge, FL

Home2 Suites Sarasota I-75 Bee Ridge, FL
Sarasota
  • Relaxing outdoor oasis with lounge chairs and a 9-hour daily swim window awaits guests.
HK$766
HK$865 total
includes taxes & fees
11 Oct - 12 Oct
Home2 Suites Sarasota I-75 Bee Ridge, FL
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 hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.
A multi-story hotel with a modern design, featuring balconies, a covered entrance, and lush landscaping.

5. 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.
HK$733
HK$829 total
includes taxes & fees
29 Sept - 30 Sept
Spark by Hilton Sarasota Siesta Key Gateway
A spacious lobby with a seating area, a reception desk, and a large window providing natural light.

6. Caretta Landing Sarasota, an Ascend Collection Hotel

Caretta Landing Sarasota, an Ascend Collection Hotel
Fruitville
  • Dive into a heated outdoor pool paradise with poolside cocktail service and plush loungers at this immaculate Sarasota retreat.
HK$727
HK$865 total
includes taxes & fees
6 Oct - 7 Oct
Caretta Landing Sarasota, an Ascend Collection Hotel
A hotel pool area with lounge chairs and a covered seating area.
A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.
A spacious lobby with a reception desk, seating area, and decorative wall art.
A hotel room with two beds, a kitchenette, a TV, and a desk.

7. Carlisle Inn

Carlisle Inn
Pinecraft
  • Refresh yourself poolside under the Florida sun in this tranquil Pinecraft sanctuary.
HK$1,065
HK$1,203 total
includes taxes & fees
11 Oct - 12 Oct
Carlisle Inn
A swimming pool with a 5 FT 15M depth marker, surrounded by palm trees and a fenced area with lounge chairs.
An aerial view of a coastal resort with a long sandy beach, clear turquoise waters, and a mix of residential and hotel buildings.
A modern interior with a wooden dining table, blue sofa, and a TV mounted on the wall.
A hotel room with two beds, a nightstand with a lamp, and a carpeted floor.

8. Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge
Sarasota
  • Poolside paradise features comfortable loungers and a rejuvenating hot tub at this newly remodeled hotel with excellent service.
HK$733
HK$829 total
includes taxes & fees
28 Sept - 29 Sept
Hampton Inn Sarasota - I-75 Bee Ridge
An indoor swimming pool with clear lane markings, a tiled wall, and a seating area with a colorful mosaic pattern.
A multi-level atrium with a central seating area, glass railings, and a large black door.
A multi-level atrium with glass railings and a central skylight.
A circular fire pit surrounded by a wooden pergola with cushioned seating and colorful pillows.

9. DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport
Sarasota
  • Make a splash in the stylish indoor pool with year-round comfort at this upscale airport hotel.
HK$830
HK$938 total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Sarasota Bradenton Airport
A pool area with lounge chairs and umbrellas, surrounded by a fence and palm trees.
A hotel lobby with two brown sofas, a red sofa with gold patterns, a coffee station, and a reception desk.
A hotel room with two beds, a sofa, a desk, a TV, and a painting on the wall.
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

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.
HK$652
HK$737 total
includes taxes & fees
23 Sept - 24 Sept
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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"El sitio esta muy bien ubicado ,las piscinas hermosas,la habitación se encontraba bien limpia realmente voy a repetir la visita porque vale la pena."
Amaya 2-night trip
Posted 1 hour ago
Tropical Beach Resorts
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"We had such an amazing stay at Tropical Cottages! I could not recommend this place enough and definitely see this becoming a regular vacation spot for our family. First off, the location could not be any better. You are literally steps away from the beach and a ton of restaurants! We had our 1 1/2 year old and carried him everywhere, so it was perfect to not have to wander too far to find what we needed. The beach here is UNBELIEVABLE. We grew up in South Florida and have been to several beaches throughout the state. This is 100% my favorite! The rooms were clean, comfy, and cozy. My only complaint (gotta have at least one!) is I wish there were hoses or showers outside the rooms so we could get the sand off our feet before going inside. Such a minor complaint. Everything was just so perfect about our stay and we cannot wait to return! Cannot recommend enough!!"
Alexandra 2-night trip
Posted 4 hours ago
Tropical Breeze Resort
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Perfect location for our travel baseball team for the weekend. Close enough to the multiple locations we played at and near many different food options. The staff was nice and inviting. Breakfast was good and the hotel itself was well maintained."
Carrie 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Internet was very spotty. Not good in room, had to go to pool to stay connected. Otherwise great."
Paulette 3-night trip
Posted 17 hours ago
Siesta Key Beach Resort and Suites
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Staff were friendly and the property was clean. No complaints. More info on the pool at check in would have been nice, but overall a great stay"
Trevor 1-night trip
Posted 21 hours ago
Golden Host Resort - Sarasota
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good
"The room was clean, air conditioning was great, pool was also clean. Will say not enough towels in the room but overall good"
Tyrin 3-night trip
Posted 1 day ago
Spark by Hilton Sarasota Siesta Key Gateway
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

10/10 Excellent
"We love the hospitality and everyone was so kind. It has been an extraordinary experience with all the staff at The Ritz Charlton. Thank You!!!"
Loida 2-night trip
Posted 2 days ago
The Ritz-Carlton, Sarasota

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.

Explore a world of travel with Expedia