Find Hotels with a Pool in Osprey, FL

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Hotels with a Pool

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Osprey hotels with a pool

Outdoor dining
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
2.5 star property
Osprey
8.8 out of 10, Excellent, (1120)
"Great place for our family to stay! "
United States
Jordan
The price is ￥21,986
￥24,845 total
includes taxes & fees
Dec 29 - Dec 30
Casey Key Resorts - Mainland
Outdoor pool
Sun Coast Inn

Sun Coast Inn

Sun Coast Inn
2.5 star property
Englewood South
7.8 out of 10, Good, (863)
"Room was was good. Location was good."
United States
Brian
The price is ￥14,224
￥16,641 total
includes taxes & fees
Dec 29 - Dec 30
Sun Coast Inn
Outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas, sun loungers
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
2.0 star property
Venice Island
7.6 out of 10, Good, (1005)
"Very clean & the staff are super nice 😊 "
United States
Jean
The price is ￥10,803
￥12,748 total
includes taxes & fees
Dec 30 - Dec 31
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
Outdoor pool
Motel 6 Venice, FL

Motel 6 Venice, FL

Motel 6 Venice, FL
2.0 star property
Gateway
8.2 out of 10, Very Good, (365)
"Great Staff, Good Room"
United States
Joseph
The price is ￥9,157
￥10,623 total
includes taxes & fees
Dec 29 - Dec 30
Motel 6 Venice, FL
Free daily buffet breakfast
Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
2.5 star property
Nokomis
9.6 out of 10, Exceptional, (361)
"Very clean hotel. Great service and very clean and comfortable room"
United States
Iris
The price is ￥18,475
￥20,876 total
includes taxes & fees
Dec 30 - Dec 31
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
2 outdoor pools, a heated pool
Siesta Key Palms Resort

Siesta Key Palms Resort

Siesta Key Palms Resort
3.5 star property
Sarasota
9.2 out of 10, Wonderful, (1000)
"Tiki bar was a definite plus"
United States
thomas
The price is ￥12,716
￥22,331 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Siesta Key Palms Resort
Outdoor pool, a heated pool, sun loungers
Inn at the Beach

Inn at the Beach

Inn at the Beach
3.0 star property
Venice Island
9.8 out of 10, Exceptional, (1005)
"Very nice employees, great continental breakfast and very close to everything "
United States
Joseph
The price is ￥26,178
￥33,651 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Inn at the Beach
Outdoor pool, a heated pool
Kompose Boutique Hotel

Kompose Boutique Hotel

Kompose Boutique Hotel
3.0 star property
Sarasota
9.2 out of 10, Wonderful, (4809)
"Clean room, friendly staff, good breakfast 😋 "
United States
Jorge
Kompose Boutique Hotel
Seasonal outdoor pool
Hampton Inn & Suites North Port

Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
North Port
9.4 out of 10, Exceptional, (611)
"Very clean and very friendly staff! "
United States
Megan
The price is ￥24,265
￥27,419 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites North Port
Outdoor pool, pool umbrellas, sun loungers
Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice
2.5 star property
Venice
9.0 out of 10, Wonderful, (1002)
"The room was spotless and the staff were terrific."
United States
Lorraine
The price is ￥19,845
￥22,425 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Best Western Plus Ambassador Suites Venice
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.
View all properties

Top Osprey Hotel Reviews

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Expensive breakfast for food not worthy "
wilma 1-night trip
Posted 1 day 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 free self parking. Kompose Boutique Hotel: Offers a snack bar/deli, a pool, and complimentary wireless internet access. Tropical Beach Resorts: Aparthotel, 9-minute walk from Crescent Beach. Provides free self parking, an outdoor pool, and complimentary wireless internet access. Carlisle Inn: Hotel located near Sarasota Memorial Hospital. Features buffet, an outdoor pool, and free self parking. Hibiscus Suites - Gateway to Siesta Key: Aparthotel located near Siesta Key Beach. Offers complimentary wired internet access, an outdoor pool, and free self parking.
What is there to see and do in Osprey?
Explore places like Siesta Key Beach, Lido Beach, and St. Armands Circle 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.