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 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
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 restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.
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.
$106 nightly
$119 total
Sep 13 - Sep 14
Total with taxes and fees
Casey Key Resorts - Mainland
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.

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.
$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 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.
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.
$93 nightly
$106 total
Sep 14 - Sep 15
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A modern hotel room with a desk, office chair, sofa, TV, and dining area.
A modern bathroom with a shower, a sink, and a mirror.

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.
$87 nightly
$98 total
Sep 16 - Sep 17
Total with taxes and fees
Holiday Inn Express Sarasota East - I-75 by IHG
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.

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.
$105 nightly
$119 total
Sep 13 - Sep 14
Total with taxes and fees
Siesta Key Palms Resort
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.
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.
A living room with a TV, white cabinets, a sofa, and a balcony with a view.

6. 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
Sep 13 - Sep 14
Total with taxes and fees
Escape Coastal Resort on Casey Key
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.

7. 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 13 - Sep 14
Total with taxes and fees
Inn at the Beach
A swimming pool with a brick border, surrounded by lounge chairs and a fence.
A hotel room with two beds, a nightstand, a lamp, and a large painting of a pier and sunset.
A spacious lobby with a reception desk, seating area, and large windows.
A room with two black leather chairs, a round table, and a lamp.

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 swimming pool area with a tiled deck, lounge chairs, and a covered seating area.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, and a view of the outdoors.
A spacious lobby with a central seating area, a kitchen in the background, and a large chandelier.
A spacious living area with a wooden floor, teal upholstered furniture, and a central coffee table.

9. Hampton Inn & Suites Venice Bayside South Sarasota

Hampton Inn & Suites Venice Bayside South Sarasota
Gateway
  • Sun-drenched relaxation awaits at this Venice hotel's outdoor pool, complemented by beach proximity and modern comforts.
$114 nightly
$129 total
Sep 20 - Sep 21
Total with taxes and fees
Hampton Inn & Suites Venice Bayside South Sarasota
A pool area with lounge chairs and umbrellas, surrounded by a fence and palm trees.
A hotel room with two beds, a sofa, a desk, a TV, and a painting on the wall.
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.

10. 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.
$88 nightly
$100 total
Sep 13 - Sep 14
Total with taxes and fees
Best Western Plus Ambassador Suites Venice
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

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"The staff was very helpful and attentive."
Jose 2-night trip
Posted 6 hours ago
Siesta Key Beach Resort and Suites
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"With in walking of everything. Easy going place. Excellent coffee, relaxing pool."
Dawn 2-night trip
Posted 9 hours ago
Tropical Breeze Resort
Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Q no lo duden q es un lugar espectacular y muy acogedor"
Yeisy 3-night trip
Posted 15 hours ago
Tropical Beach Resorts
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 2 days ago
DoubleTree by Hilton Sarasota Bradenton Airport

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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