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

Find Hotels with a Pool in Osprey, FL

  • 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
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

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$2,479
NT$3,138 total
includes taxes & fees
Sep 13 - Sep 14
Casey Key Resorts - Mainland

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

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$2,949
NT$3,333 total
includes taxes & fees
Sep 14 - Sep 15
Spark by Hilton Sarasota Siesta Key Gateway

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 20 - Sep 21
Holiday Inn Express Sarasota East - I-75 by IHG

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$1,806
NT$3,645 total
includes taxes & fees
Sep 13 - Sep 14
Siesta Key Palms Resort

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$2,584
NT$4,881 total
includes taxes & fees
Sep 13 - Sep 14
Escape Coastal Resort on Casey Key

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$3,052
NT$4,269 total
includes taxes & fees
Sep 13 - Sep 14
Inn at the Beach

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 14 - Sep 15
Days Inn by Wyndham Sarasota I-75

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$3,596
NT$4,064 total
includes taxes & fees
Sep 17 - Sep 18
Hampton Inn & Suites Venice Bayside South Sarasota

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$2,780
NT$3,141 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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"We had a wonderful stay! The room was very clean and comfortable! The property is beautiful and very well maintained. We are looking forward to coming back and staying again!"
Juanita 4-night trip
Posted 1 hour ago
Tropical Beach Resorts
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"La ubicación de la propiedad es privilegiada para moverse a Siesta Beach y tiene lugares cerca para comer y beber, excelente lugar para visitar, por su ubicación repetiría sin lugar a dudas. La única observación que tengo es que el agua de la ducha no calentó en los días que estuvimos, tuvimos que bañarnos con agua fría y eso deberían revisarlo, además la oferta de desayuno es luy limitada, por lo demás nos encantó el lugar."
Sadan Ruben 2-night trip
Posted 1 hour ago
Spark by Hilton Sarasota Siesta Key Gateway
Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Spacious room, very clean, Great staff, very professional."
Laura 4-night trip
Posted 2 hours ago
Hyatt Place Sarasota/Bradenton Airport
Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"The room was immaculate; the staff was very helpful and I can't wait to return!"
Carolyn 2-night trip
Posted 3 hours ago
Siesta Key Palms Resort
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Personal muy amables, habitaciones muy limpias y con todo lo necesario. Súper tranquilo y cerca a la playa q es hermosa !! Volveremos!!"
Alcira 2-night trip
Posted 4 hours ago
Siesta Key Beach Resort and Suites
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Nice clean place. Friendly helpful staff!"
Shawn 3-night trip
Posted 11 hours ago
Golden Host Resort - 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 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.

Explore a world of travel with Expedia