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 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.
A balcony with two black chairs, a white railing, and a view of palm trees and a building in the background.
A modern bedroom with a bed, a desk, and a sofa.
A pathway flanked by palm trees and a building with a covered patio area.

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.
$118 nightly
$134 total
Oct 26 - Oct 27
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 hotel reception area with a wooden reception desk, a large abstract mural, and a seating area with a view of greenery outside.
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.
$106 nightly
$120 total
Oct 31 - Nov 1
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
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 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.
A wooden deck with chairs and a table overlooking a body of water.

3. 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 rectangular swimming pool with white lounge chairs on both sides, surrounded by palm trees and a wooden fence.
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.
A modern living room with a grey sofa, a blue patterned armchair, a dining area with wicker chairs, and a view through glass doors to an outdoor patio.

4. 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.
$146 nightly
$165 total
Oct 29 - Oct 30
Total with taxes and fees
Escape Coastal Resort on Casey Key
A pool area with a waterfall feature, lounge chairs, and palm trees.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.
A covered patio with a brick floor, wicker furniture, and tropical plants.
A beach with white sand, clear blue water, and a few beach umbrellas.

5. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
$163 nightly
$184 total
Nov 25 - Nov 26
Total with taxes and fees
Tropical Beach Resorts
A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
A modern lobby with a sofa, chairs, a desk, and a map mural on the wall.
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.

6. 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.
$105 nightly
$119 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
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 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.
A hotel room with two beds, a nightstand, and a desk.

7. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
$103 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A swimming pool with lounge chairs and palm trees, surrounded by string lights.
A covered outdoor area with a pool, lounge chairs, and a wooden deck.
A bar area with a wooden ceiling, bar stools, and a neon sign.
A bedroom with a bed, bedside tables, a desk, and a chair.

8. 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.
$102 nightly
$115 total
Nov 15 - Nov 16
Total with taxes and fees
Siesta Key Palms Resort
A beach with white lounge chairs and striped umbrellas.
A kitchen with a built-in microwave, a small refrigerator, and a wooden shelf with a coffee maker and other items.
A bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.
A modern house with a patio, outdoor seating, and a view of the ocean.

9. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
$176 nightly
$199 total
Nov 19 - Nov 20
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 room with a sofa, a desk, a lamp, a television, and a window with patterned curtains.
A compact kitchen with a microwave, sink, and dishwasher.
A hotel with a covered outdoor seating area, palm trees, and a sign reading "HOME 2".

10. 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.
$120 nightly
$135 total
Nov 15 - Nov 16
Total with taxes and fees
Home2 Suites by Hilton Nokomis Sarasota Casey Key
View all properties

Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
Beach
5 stars

Find out more about Osprey

Discover top Osprey attractions

Osprey offers a delightful blend of natural beauty and engaging activities for travelers seeking adventure and relaxation. Start your journey at the scenic waterfront, where you can enjoy a leisurely stroll along the shoreline, taking in mesmerizing views of the Gulf of Mexico. For those interested in outdoor pursuits, the nearby nature preserve is perfect for birdwatching and exploring lush trails that wind through diverse ecosystems. History enthusiasts will appreciate the charming local heritage, with unique architecture and cultural sites that tell the story of the area’s past. Families can enjoy a day of exploration at the local parks, which feature spacious picnic areas and playgrounds, ensuring a fun-filled day for kids and adults alike. Finally, don’t miss the local artisan shops, where you can find one-of-a-kind crafts and souvenirs that make for perfect keepsakes from your travels. With a variety of accommodations nearby, you can relax in comfort while soaking up the vibrant atmosphere of Osprey.

Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"The pool area is wonderful and very well maintained!"
Beatriz 2-night trip
Posted 10 hours ago
Golden Host Resort - Sarasota
Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
""The receptionist's office was very customer-service-oriented and helpful with our needs. They communicated quickly via text and phone. The cleaning ladies were exceptional with their service and flexibility. This place is definitely 5-star in service and cleanliness, and the location was half a block from the beach and a block from the main road. I loved that 10 p.m. to 8 a.m. was quiet time on the premises. When we visit Siesta Key again, we will be staying here.""
Raul Aponte 4-night trip
Posted 10 hours ago
Tropical Beach Resorts
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Completely enjoyed our stay here. Very clean friendly and helpful staff. Beach is close. Looking forward to coming back."
Nancy 5-night trip
Posted 11 hours ago
Siesta Key Beach Resort and Suites
Lido Beach Resort

Lido Beach Resort

8/10 Good
"Our only disappointment with the resort was our room which was located on the ground floor of the original older building. While the room was clean and well taken care of by the maid service we would have preferred to have stayed in the newer tower next door, but we were not aware of the differences between the buidings wehen we booked the room."
Bob 3-night trip
Posted 14 hours ago
Lido Beach Resort
Cirque St. Armands Beachside

Cirque St. Armands Beachside

10/10 Excellent
"Great stay"
Christopher 2-night trip
Posted 15 hours ago
Cirque St. Armands Beachside
The Westin Sarasota

The Westin Sarasota

8/10 Good
"Everything was great"
Mykhaylo 5-night trip
Posted 15 hours ago
The Westin Sarasota
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

10/10 Excellent
"It was nice and clean. Much more affordable. Could use more of a selection of bourbon."
Nathan 1-night trip
Posted 3 days ago
EVEN Hotel Sarasota-Lakewood Ranch by IHG
Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"We cannot say enough good things about our stay here. The villa we stayed at was clean and had lots of amenities we didn't anticipate. The staff was amazing and helpful. Other than updating the bar and maintenance was the only hiccup. The location is really great. Just a small walk across the bridge to Siesta Key Beach. Lots of great eating establishments walking distance from Hotel. We are already looking to re-book early next year. This place is a hidden gem. Thank you Siesta Key Palms resort. Darin"
Darin 4-night trip
Posted 3 days ago
Siesta Key Palms Resort
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Deluxe room was nice and spacious. Very clean. Nice pool and bar. Pizza was delicious!"
Christine 5-night trip
Posted 4 days ago
Casey Key Resorts - Mainland

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 from $69 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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