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
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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 pathway flanked by palm trees and a building with a covered patio area.
A modern bedroom with a bed, a desk, and a sofa.

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.
$89 nightly
$100 total
Aug 31 - Sep 1
Total with taxes and fees
Casey Key Resorts - Mainland
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A Holiday Inn Express hotel with a covered entrance, palm trees, and a well-lit facade.
A spacious hotel lobby with a dining area, seating, and artwork on the walls.
A hotel room with two beds, a desk with a chair, a television, and a window with blinds.

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.
$77 nightly
$87 total
Sep 3 - Sep 4
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.
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.
A hotel lobby with a reception desk, a refrigerator with beverages, and a microwave.

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.
$91 nightly
$103 total
Aug 31 - Sep 1
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 a grey sofa, a small round table, a bed, and three framed pictures on the wall.
A hotel breakfast area with a self-service station, a refrigerator with beverages, and a wall-mounted sign.
A hotel room with two beds, a nightstand, and a desk.

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.
$89 nightly
$101 total
Sep 20 - Sep 21
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
A pool area with a waterfall feature, lounge chairs, and palm trees.
A covered patio with a brick floor, wicker furniture, and tropical plants.
A modern kitchen with white cabinets, a central island, and a dining area with a table and chairs.
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.
$134 nightly
$152 total
Aug 31 - Sep 1
Total with taxes and fees
Tropical Beach Resorts
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 nighttime view of a tropical resort with a water feature, palm trees, and ambient lighting.

6. 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.
$122 nightly
$137 total
Sep 3 - Sep 4
Total with taxes and fees
Siesta Key Palms Resort
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A round table with two green placemats, a yellow napkin, and a glass vase with a pink flower.
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.

7. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
$116 nightly
$131 total
Sep 16 - Sep 17
Total with taxes and fees
Inn at the Beach
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 sandy pathway leading to a beach with a clear view of the ocean.
A bedroom with a bed, a wooden sign above the bed, a nightstand, and a view of a garden.

8. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
$122 nightly
$138 total
Sep 23 - Sep 24
Total with taxes and fees
Casey Key Resorts - Beachfront
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.

9. 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.
$63 nightly
$71 total
Sep 7 - Sep 8
Total with taxes and fees
Days Inn by Wyndham Sarasota I-75
A pool area with lounge chairs and a brick pathway.
A clear turquoise sea with people swimming and a boat in the distance.
A living room with a brown leather sofa, a wicker chair, a glass coffee table, and a dining area with a white table and chairs.
A living room with a sofa, a television, a coffee table, and a view of a pool.

10. Siesta Palms By the Beach

Siesta Palms By the Beach
South Village
$164 nightly
$186 total
Sep 2 - Sep 3
Total with taxes and fees
Siesta Palms By the Beach
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

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"La atención de las personas en el hotel"
Erick 1-night trip
Posted less than an hour ago
Lido Beach Resort
Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"N/A"
Silvia 1-night trip
Posted 2 hours ago
Tropical Beach Resorts
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"This place is not new but has really been maintained well and has such a fun, retro motif. The rooms are HUGE and the cutest little mini fridge and matched microwave. The AC was great and beds were comfortable. The Bahi Hut bar had really nice drinks. Pool is very relaxed area. We really loved it! Sorry we were only there 1 night."
Cathy 1-night trip
Posted 4 hours ago
Golden Host Resort - Sarasota
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Excellent location, short walk yo the beach. The pool and hot tub were great. Staff was friendly and helpful. Would definitely stay again!"
Jill 2-night trip
Posted 5 hours ago
Siesta Key Beach Resort and Suites
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Beautiful hotel with road side parking to watch the planes land and take off. Comfy beds and pillows."
Kristina 1-night trip
Posted 1 day ago
DoubleTree by Hilton Sarasota Bradenton Airport
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

10/10 Excellent
"I had an excellent experience from the moment I arrived at the hotel. The staff were incredibly polite, friendly, and welcoming. I immediately felt comfortable and at home. Thank you for making my stay such a warm and pleasant experience!"
Rosse 3-night trip
Posted 9 days ago
The Ritz-Carlton, Sarasota

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 $71 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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