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
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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 modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.

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.
$102 nightly
$116 total
Sep 19 - Sep 20
Total with taxes and fees
Casey Key Resorts - Mainland
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A modern hotel room with a desk, office chair, sofa, TV, and dining area.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A modern bathroom with a shower, a sink, and a mirror.

2. 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.
$84 nightly
$95 total
Sep 13 - Sep 14
Total with taxes and fees
Holiday Inn Express Sarasota East - I-75 by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a fence.
An outdoor patio with a fire feature, seating, and a bar area.
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.

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.
$93 nightly
$106 total
Sep 13 - Sep 14
Total with taxes and fees
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 two beds, a nightstand, and a desk.
A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.
A lobby with a blue sofa, yellow armchairs, a reception desk, and a large white pendant light.

4. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
Sarasota
  • Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
$93 nightly
$105 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A swimming pool with lounge chairs and palm trees, surrounded by string lights.
A nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.
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.

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.
$100 nightly
$113 total
Sep 17 - Sep 18
Total with taxes and fees
Siesta Key Palms Resort
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A lifeguard tower with a blue roof and white walls, situated on a sandy beach with clear blue water in the background.
A hotel with a palm tree entrance, a neon sign, and a tiled roof.
A round table with two green placemats, a yellow napkin, and a glass vase with a pink flower.

6. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
$126 nightly
$143 total
Sep 17 - Sep 18
Total with taxes and fees
Inn at the Beach
A pool area with a waterfall feature, lounge chairs, and palm trees.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
A pathway lined with palm trees and tropical plants, leading to a building with a white facade.
A beach with white sand, clear blue water, and a few beach umbrellas.

7. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
$158 nightly
$179 total
Sep 27 - Sep 28
Total with taxes and fees
Tropical Beach Resorts
A swimming pool with a brick border, surrounded by lounge chairs and a fence.
A room with two black leather chairs, a round table, and a lamp.
A spacious lobby with a reception desk, seating area, and large windows.
A hotel room with two beds, a nightstand, a lamp, and a large painting of a pier and sunset.

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.
$60 nightly
$68 total
Sep 13 - Sep 14
Total with taxes and fees
Days Inn by Wyndham Sarasota I-75
A beach with white lounge chairs and striped umbrellas.
A sandy pathway leading to a beach with a clear 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 bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.

9. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
$141 nightly
$160 total
Sep 23 - Sep 24
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 modern kitchen with a stainless steel refrigerator, a built-in microwave, a dishwasher, and wooden cabinetry.
A hotel room with a sofa, a desk, a lamp, a television, and a window with patterned curtains.

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.
$130 nightly
$147 total
Oct 6 - Oct 7
Total with taxes and fees
Home2 Suites by Hilton Nokomis Sarasota Casey Key
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Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
Beach
5 stars

Top Osprey Hotel Reviews

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Great easy check in friendly"
Curtis 1-night trip
Posted 3 hours ago
Hyatt Place Sarasota/Bradenton Airport
The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Great property and staff. We enjoyed our service for breakfast with Belinda :)"
Miranda 5-night trip
Posted 7 hours ago
The Westin Sarasota
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"My room was spacious clean and comfortable. My husband said it was wonderful."
Marc 1-night trip
Posted 18 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Super convenient location. We love the fact that you just walk to the beach anytime you want. You can also walk to the villa where you fund all kind of restaurants and stores."
WALDO 3-night trip
Posted 18 hours ago
Tropical Breeze Resort
Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"So beautiful! All staff were SO helpful and very friendly. The first day, the adult pool was quite crowded and alcohol was flowing so it got quite noisy, but the rest of the week was perfect."
Cheryl 7-night trip
Posted 19 hours ago
Lido Beach Resort

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 $68 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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