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

Find Hotels with a Pool in Osprey Village, 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 Village Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Osprey Village hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.
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.
An outdoor patio with a fire feature, seating, and a bar area.

1. 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.
₩127,701
₩144,302 total
includes taxes & fees
Oct 27 - Oct 28
Spark by Hilton Sarasota Siesta Key Gateway
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 a grey sofa, a small round table, a bed, and three framed pictures on the wall.
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.
A hotel room with two beds, a nightstand, and a desk.

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.
₩134,201
₩151,648 total
includes taxes & fees
Oct 29 - Oct 30
Comfort Suites Sarasota - Siesta Key
A swimming pool with a 5 FT 15M depth marker, surrounded by palm trees and a fenced area with lounge chairs.
A modern kitchen area with a wooden counter, a coffee machine, and a fruit display.
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.

3. 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.
₩134,201
₩151,648 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Sarasota - I-75 Bee Ridge
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building with a 'HOTEL' sign.
A modern hotel room with a desk, office chair, sofa, TV, and dining area.
A hotel room with two beds, a desk, a chair, a TV, and a window with blinds.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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.
₩134,436
₩151,913 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Inn Express Sarasota East - I-75 by IHG
A swimming pool with a 3ft 6in depth marker, surrounded by lounge chairs and palm trees.
Restaurant
A hotel room with a round wooden table, two beige armchairs, a large painting of a forest, a ceiling light, and a window with curtains.
A lobby with a reception desk, seating area, and a decorative wall.

5. Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice
Venice
  • Soak up the sun at this Venice Beach hotel's inviting outdoor pool with loungers and umbrellas.
₩118,969
₩134,436 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Venice
A hotel pool area with lounge chairs and a covered seating area.
A spacious lobby with a reception desk, seating area, and decorative wall art.
A spacious kitchen with a central island, built-in appliances, and a large window providing a view of the outdoors.
A hotel with a central entrance, multiple floors, and a landscaped front yard with palm trees.

6. Carlisle Inn

Carlisle Inn
Pinecraft
  • Refresh yourself poolside under the Florida sun in this tranquil Pinecraft sanctuary.
₩189,990
₩214,690 total
includes taxes & fees
Nov 1 - Nov 2
Carlisle Inn
A pool area with lounge chairs and umbrellas, surrounded by a fence and palm trees.
A hotel with a covered entrance, a landscaped driveway, and palm trees.
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.
A hotel lobby with two brown sofas, a red sofa with gold patterns, a coffee station, and a reception desk.

7. 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.
₩104,101
₩117,634 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Plus Ambassador Suites Venice
A resort with a pool, sun loungers, and a wooden deck.
A pathway flanked by palm trees and a building with a covered patio area.
A modern bedroom with a bed, a desk, and a sofa.
A modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.

8. 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.
₩140,519
₩177,841 total
includes taxes & fees
Oct 25 - Oct 26
Casey Key Resorts - Mainland
A pool area with a waterfall feature, lounge chairs, and palm trees.
A beach with white sand, clear blue water, and a few beach umbrellas.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
A covered patio with a brick floor, wicker furniture, and tropical plants.

9. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
₩175,344
₩232,732 total
includes taxes & fees
Oct 22 - Oct 23
Tropical Beach Resorts
Pool
A hotel room with a sofa, a bed, a desk with a lamp, a TV, and framed pictures on the wall.
A spacious dining area with multiple tables and chairs, a kitchen area with appliances, and large windows allowing natural light.
An outdoor patio with wicker furniture, a grill, and lush tropical plants.

10. Coral Pointe Sarasota, an Ascend Collection Hotel

Coral Pointe Sarasota, an Ascend Collection Hotel
Fruitville
  • Make a splash with a stylish outdoor pool oasis and tantalizing poolside restaurant service.
₩123,322
₩146,807 total
includes taxes & fees
Oct 27 - Oct 28
Coral Pointe Sarasota, an Ascend Collection Hotel
View all properties

Choose what matters most at hotels with a pool in Osprey Village

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Osprey Village Hotel Reviews

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"This place was great! You are transported back to the 50s and 60s with the full Tiki Vibe! The rooms are clean and beds comfortable. The neighborhood is in the midst of a resurgence so it’s not going to be long before this area is much more expensive! The staff is outstanding and the Bahi hut is a great place to unwind! It’s not the luxury hotels that are right up the road, but the quirkiness of this place more than makes up for it and the staff will likely actually know your name! Thank you to everyone on the staff for a great stay!"
Zachary 3-night trip
Posted 8 hours ago
Golden Host Resort - Sarasota
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Amazing stay"
Jose Luis 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport
Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"Cool spot with a very chill vibe. Recommended as an alternate to massive hotels. They make the most of their little slice of paradise. The staff is amazing and extremely helpful. We will be back for sure."
Eric 1-night trip
Posted 21 hours ago
Siesta Key Palms Resort
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

10/10 Excellent
"Best hotel I’ve ever stayed at. The staff was amazing. Ready to help at all times! The spa was fantastic, as well as the Beach Club!"
Michael 3-night trip
Posted 1 day ago
The Ritz-Carlton, Sarasota
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"The restaurant and bar were very nice. We enjoyed the food and live music. The pool area was also very nice. The rooms had beach chairs and a cooler which was very nice. The beach was just steps away from the hotel which is amazing. All the staff at the hotel were very accommodating. We will be back again."
Adam 2-night trip
Posted 1 day ago
Siesta Key Beach Resort and Suites

Frequently asked questions

What are some hotels with pools in Osprey Village?
Kompose Boutique Hotel: Features a snack bar/deli, a pool, and complimentary wireless internet access. Tropical Beach Resorts: Aparthotel, 10-minute walk from Crescent Beach. Offers free self parking, 2 outdoor pools, and complimentary wireless internet access. The Westin Sarasota: Hotel located near Lido Beach. Provides 2 restaurants, an outdoor pool, and a full-service spa. Siesta Key Beach Resort and Suites: Resort, 1-minute walk from Siesta Key Beach. Features complimentary bicycles, a pool, and complimentary wireless internet access. Carlisle Inn: Hotel located near Sarasota Memorial Hospital. Offers buffet, an outdoor pool, and free self parking.
What is there to see and do in Osprey Village?
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 Point of Rocks.
When is the best time to book a hotel with a pool in Osprey Village?
Taking into account the local weather in Osprey Village 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 Village is 44 inches.

Explore a world of travel with Expedia