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 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Osprey hotels with a pool

A resort with a pool, sun loungers, and a wooden deck.
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.
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.
$102 nightly
$115 total
Sep 30 - Oct 1
Total with taxes and fees
Casey Key Resorts - Mainland
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 lobby with a reception desk, a refrigerator with beverages, and a microwave.

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.
$97 nightly
$110 total
Oct 1 - Oct 2
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
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.

3. 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
Oct 6 - Oct 7
Total with taxes and fees
Siesta Key Palms Resort
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 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.
A hotel room with a grey sofa, a small round table, a bed, and three framed pictures on the wall.

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.
$97 nightly
$110 total
Oct 6 - Oct 7
Total with taxes and fees
Comfort Suites Sarasota - Siesta 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.
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.

5. 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 6 - Oct 7
Total with taxes and fees
Escape Coastal Resort on Casey Key
A hotel with a swimming pool, lounge chairs, and a covered area with umbrellas.
A hotel room with two beds, a desk, a chair, a TV, and a window with blinds.
A modern bathroom with a shower, a sink, and a mirror.
A coffee station with two coffee machines and a variety of coffee pods and cups.

6. 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.
$76 nightly
$86 total
Oct 27 - Oct 28
Total with taxes and fees
Holiday Inn Express Sarasota East - I-75 by IHG
A swimming pool with a white pergola overhead, surrounded by lounge chairs and umbrellas.
A pathway leading to a white staircase surrounded by lush greenery and palm trees.
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.

7. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
$125 nightly
$141 total
Sep 30 - Oct 1
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.
$62 nightly
$70 total
Sep 30 - Oct 1
Total with taxes and fees
Days Inn by Wyndham Sarasota I-75
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 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.

9. 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 30 - Oct 1
Total with taxes and fees
Tropical Beach Resorts
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 modern house with a patio, outdoor seating, and a view of the ocean.

10. Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront
Casey Key
$149 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Casey Key Resorts - Beachfront
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
"Great location within walking distance to everything we needed. Live music playing in the tiki bar as well as several other nearby restaurants/bars. Right across the street from beach access to the most beautiful beach ever. We loved our stay!"
David 2-night trip
Posted 3 hours ago
Siesta Key Beach Resort and Suites
Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Beautiful property close to everything we wanted to do."
Lara 1-night trip
Posted 8 hours ago
Tropical Breeze Resort
Cirque St. Armands Beachside

Cirque St. Armands Beachside

10/10 Excellent
"The location is great. The hotel is extremely clean, no a speck of dust. Everything is in perfect repair. The pictures on line do not do it justice. One of the nicest hotels I have stayed in"
Kate 2-night trip
Posted 17 hours ago
Cirque St. Armands Beachside
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"1"
Daniel 2-night trip
Posted 19 hours ago
Spark by Hilton Sarasota Siesta Key Gateway
Lido Beach Resort

Lido Beach Resort

8/10 Good
"The staff, location and amenities are excellent. If you stay here get a room that’s facing the ocean or the courtyard. Our room was facing the parking lot and was on the first level. I felt it was a little over priced given its location in resort."
jeff 3-night trip
Posted 23 hours ago
Lido Beach Resort
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Amazing staff! Very helpful all around amazing stay"
Christopher 2-night trip
Posted 2 days ago
Golden Host Resort - 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 $70 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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