Find Hotels with a Pool in Osprey, FL

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Osprey Hotels with a Pool

Top Osprey Hotels with a Pool

Bentley's Boutique Hotel, BW Premier Collection
Outdoor pool, free cabanas, pool umbrellas

Bentley's Boutique Hotel, BW Premier Collection

2.5 star property
8.6 out of 10, Excellent, (1000)
"Check in was backed up a bit at 7:00 p.m. Room was nice. Bar area outside was enjoyable with live music..drinks..the bright moon. Enjoyed the pool ...good temperature. Breakfast was good. Love the Coffee machine in the lobby area."
Bentley's Boutique Hotel, BW Premier Collection
Casey Key Resorts - Mainland
Outdoor dining

Casey Key Resorts - Mainland

2.5 star property
8.6 out of 10, Excellent, (1049)
"The room was very cleaned and spacious nice balcony view as well . "
The price is SAR 465
SAR 525 total
includes taxes & fees
31 Aug - 1 Sep
Casey Key Resorts - Mainland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"We had a wonderful stay here everything about the property was great one minor gripe was the amount of glass being allowed in the pool and also security didn’t do enough to Stop it a huge family arrived one day eating drinking in the pool if you have pool rules stick to them . Get rid of wristbands "
Warren 7-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 free self parking. Kompose Boutique Hotel: Offers a snack bar/deli, a pool, and free self parking. Tropical Beach Resorts: Aparthotel, 9-minute walk from Crescent Beach. Provides free self parking, an outdoor pool, and sun loungers. The Westin Sarasota: Hotel located near Lido Beach. Features 2 restaurants, an outdoor pool, and a full-service spa. Embassy Suites by Hilton Sarasota, FL: Hotel located near Lido Beach. Offers on-the-go, an outdoor 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.