Find Hotels with a Pool in Osprey, FL

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Check availability on Osprey Hotels with a Pool

Tonight
Mar 5 - Mar 6
Tomorrow
Mar 6 - Mar 7
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

Our top choices for Osprey hotels with a pool

Premium Pool View King Suite | View from room

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
Osprey
8.8 out of 10, Excellent, (1,147 reviews)
"We loved the pool in the center of the resort."
United States
Ken
$210 nightly
The price is $237
Mar 8 - Mar 9
Total with taxes and fees
Casey Key Resorts - Mainland
Outdoor pool

Sun Coast Inn

Sun Coast Inn
2.5 star property
Englewood South
8.0 out of 10, Very Good, (907 reviews)
"Great staff, great location "
United States
gregory
$114 nightly
The price is $128
Apr 1 - Apr 2
Total with taxes and fees
Sun Coast Inn
Free daily buffet breakfast

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
2.5 star property
Nokomis
9.6 out of 10, Exceptional, (407 reviews)
"Clean, quiet, great location, exceptional staff , and excellent breakfast!"
United States
Michael
$161 nightly
The price is $182
Apr 5 - Apr 6
Total with taxes and fees
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
Outdoor pool, pool umbrellas

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota
3.0 star property
North Trail
8.4 out of 10, Very Good, (2,319 reviews)
"Really nice hotel! Clean and very comfortable beds! "
United States
Gerson
$103 nightly
The price is $117
Apr 5 - Apr 6
Total with taxes and fees
Golden Host Resort - Sarasota
A heated pool

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (74 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
$323 nightly
The price is $361
Mar 7 - Mar 8
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
Outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas, sun loungers

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
2.0 star property
Venice Island
7.6 out of 10, Good, (1,015 reviews)
"The room was perfect and having doors to the courtyard made it even better, having morning coffee outside! Staff Very friendly and love how it’s located to stores and close to the beach we will be returning. "
United States
Ann
$93 nightly
The price is $106
Apr 5 - Apr 6
Total with taxes and fees
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
Outdoor pool, a heated pool, sun loungers

Inn at the Beach

Inn at the Beach
3.0 star property
Venice Island
9.8 out of 10, Exceptional, (1,003 reviews)
"Staff & location also the room was very clean & cleaned thoroughly every day"
United Kingdom
Alan
$310 nightly
The price is $351
Apr 1 - Apr 2
Total with taxes and fees
Inn at the Beach
Classic Double Room, 2 Double Beds, Refrigerator & Microwave | Terrace/patio

Sun Life Beach Hotel

Sun Life Beach Hotel
2.5 star property
Englewood Central
9.6 out of 10, Exceptional, (362 reviews)
"Room was spotless. Owner was attentive, gracious and accommodating. Would stay again."
United States
Bryan
$175 nightly
The price is $196
Mar 27 - Mar 28
Total with taxes and fees
Sun Life Beach Hotel
Exterior

Azul Resort Siesta Key

Azul Resort Siesta Key
3.0 star property
South Village
8.8 out of 10, Excellent, (59 reviews)
"Great place, would highly recommend "
United States
Joseph
$345 nightly
The price is $390
Mar 10 - Mar 11
Total with taxes and fees
Azul Resort Siesta Key
A heated pool

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (92 reviews)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
United States
Jessie
$300 nightly
The price is $335
Mar 11 - Mar 12
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub

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Top Osprey Hotel Reviews

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

2/10 Terrible
"Husband was injured when the grab bar in the shower came out of the wall"
Kris 2-night trip
Posted 5 hours ago
Hyatt Place 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 $106 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.
How can I save on a Osprey hotel with a pool with Expedia?
Before booking your Osprey hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
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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