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

Find Hotels with a Pool in Osprey, FL

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Check availability on Osprey Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.
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.
A balcony with two black chairs, a white railing, and a view of palm trees and a building in the background.

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.
$73 nightly
$83 total
Nov 2 - Nov 3
Total with taxes and fees
Casey Key Resorts - Mainland
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 lobby with a reception desk, a refrigerator with beverages, and a microwave.
An outdoor patio with a fire feature, seating, and a bar area.

2. 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.
$88 nightly
$99 total
Oct 18 - Oct 19
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
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.

3. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
$150 nightly
$170 total
Oct 19 - Oct 20
Total with taxes and fees
Tropical Beach Resorts
A swimming pool with a 3 ft 3 in depth marker, surrounded by lounge chairs and a covered seating area with a view of the water.
A sandy beach path with wooden posts and ropes, leading towards the ocean.
A spacious living area with a large window overlooking a body of water, a balcony with a view, a kitchen with a TV, and a seating area with a sofa and chairs.
A narrow stone pathway flanked by lush green plants and a wooden pergola structure.

4. Turtle Beach Resort

Turtle Beach Resort
Siesta Key
  • Private hot tubs and a serene outdoor pool await on this peaceful retreat near Turtle Beach.
$287 nightly
$321 total
Nov 1 - Nov 2
Total with taxes and fees
Turtle Beach Resort
A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
A reception area with two reception desks, a blue geometric wall design, and a wooden panel accent.
A conference room with a long table, blue chairs, framed artwork on the walls, and a Holiday Inn Express sign.
A modern bathroom with a geometric tile pattern, a large mirror, a white sink, and a glass-enclosed shower.

5. Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
Nokomis
  • Escape to a refreshing pool retreat near Venice Beach where outdoor relaxation meets coastal adventure.
$101 nightly
$114 total
Oct 19 - Oct 20
Total with taxes and fees
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
A beach with white lounge chairs and striped umbrellas.
A modern house with a patio, outdoor seating, and a view of the ocean.
A kitchen with a built-in microwave, a small refrigerator, and a wooden shelf with a coffee maker and other items.
A sandy pathway leading to a beach with a clear view of the ocean.

6. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
$129 nightly
$146 total
Nov 1 - Nov 2
Total with taxes and fees
Casey Key Resorts - Beachfront
A swimming pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows and palm trees.
A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".
A compact kitchen with a microwave, sink, and dishwasher.
Bathroom

7. Home2 Suites by Hilton Nokomis Sarasota Casey Key

Home2 Suites by Hilton Nokomis Sarasota Casey Key
Nokomis
  • Dive into aquatic bliss at this Sarasota gem with a sun-drenched pool and cozy loungers.
$122 nightly
$138 total
Nov 15 - Nov 16
Total with taxes and fees
Home2 Suites by Hilton Nokomis Sarasota Casey Key
A rectangular swimming pool with white lounge chairs on both sides, surrounded by palm trees and a wooden fence.
A marina with boats docked, surrounded by residential buildings and palm trees.
An aerial view of a coastal area with a sandy beach, a row of houses, and a clear sky.
A living room with a TV, white cabinets, a sofa, and a balcony with a view.

8. 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.
$147 nightly
$166 total
Oct 26 - Oct 27
Total with taxes and fees
Escape Coastal Resort on Casey Key
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 lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.
A hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

9. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
$101 nightly
$114 total
Oct 29 - Oct 30
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A swimming pool with lounge chairs and palm trees, surrounded by string lights.
A bedroom with a bed, bedside tables, a desk, and a chair.
A bar area with a wooden ceiling, bar stools, and a neon sign.
A covered outdoor area with a pool, lounge chairs, and a wooden deck.

10. 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.
$111 nightly
$125 total
Oct 25 - Oct 26
Total with taxes and fees
Siesta Key Palms Resort
View all properties

Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
Beach
5 stars

Top Osprey Hotel Reviews

Frequently asked questions

What are the best hotels in Osprey with outdoor pools?
Casey Key Resorts - Mainland is a fantastic option for travellers seeking a hotel in Osprey with an inviting outdoor pool. Rated 8.8 by guests, this resort creates an inviting space with its friendly and amazing staff, ensuring that travellers feel right at home.The outdoor pool is complemented by delightful amenities such as poolside cabanas that are available for free, making it a superb spot to relax and soak up the sun. Guests particularly appreciate the spacious and clean rooms, along with the excellent food offerings available on-site. The location is another highlight, providing easy access to nearby attractions that enhance your Osprey experience.For families, the pool area offers sun loungers, allowing you to unwind while the kids enjoy splashing around.
How much does a hotel with outdoor pool in Osprey cost?
Enjoy staying in a hotel in Osprey with an outdoor pool. You can find a great deal on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Osprey with outdoor pool cabanas or loungers?
Casey Key Resorts - Mainland is an excellent choice for travellers seeking outdoor relaxation in Osprey. With an excellent review rating of 8.8, this hotel offers a delightful atmosphere complemented by its inviting outdoor pool, complete with free poolside cabanas and sun loungers—superb for lounging in the Florida sun.Guests rave about the friendly and amazing staff, who go above and beyond to ensure a pleasant stay. The clean and spacious rooms are designed for comfort, making it a great option for families or those traveling with children. Additionally, the hotel features a poolside bar, allowing you to sip refreshing drinks without leaving your comfortable spot by the water.For those looking to enjoy some quality time outdoors, Casey Key Resorts - Mainland provides the ideal setting, blending convenience with a laid-back, family-friendly environment.
Which Osprey hotels offer poolside service for food and drinks?
Casey Key Resorts - Mainland is a fantastic choice for travellers seeking a delightful poolside experience in Osprey. With an impressive traveller rating of 8.8, guests rave about the friendly and amazing staff, as well as the clean and spacious rooms that ensure a comfortable stay.This hotel features an inviting outdoor pool, complete with a Poolside Bar where you can sip on refreshing drinks while enjoying the sun. Pool cabanas are available for free, offering a great spot to relax with family or friends. Sun loungers around the pool create a laid-back atmosphere, making it easy to unwind after a day of adventure.Families will appreciate the excellent food options available, enhancing the overall experience.
Is it cheaper to book flights and a Osprey hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Osprey for you.

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