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

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Osprey hotels with a pool

Premium Pool View King Suite | View from room

1. Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
Osprey
8.8 out of 10, Excellent, (1,234 reviews)
  • cleanliness
    Splash into sunshine at this Nokomis retreat featuring a heated pool and tiki bar with live music.
$108 nightly
The price is $123
Aug 5 - Aug 6
Total with taxes and fees
Casey Key Resorts - Mainland
Outdoor pool

2. Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key
3.0 star property
Sarasota
9.0 out of 10, Wonderful, (1,757 reviews)
  • cleanliness
    Plunge into poolside paradise with soothing hot tub escapes at this Sarasota retreat.
$95 nightly
The price is $108
Aug 30 - Aug 31
Total with taxes and fees
Comfort Suites Sarasota - Siesta Key
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers

3. Home2 Suites by Hilton Nokomis Sarasota Casey Key

Home2 Suites by Hilton Nokomis Sarasota Casey Key
3.0 star property
Nokomis
9.2 out of 10, Wonderful, (937 reviews)
  • cleanliness
    Dive into aquatic bliss at this Sarasota gem with a sun-drenched pool and cozy loungers.
$139 nightly
The price is $157
Aug 14 - Aug 15
Total with taxes and fees
Home2 Suites by Hilton Nokomis Sarasota Casey Key
BBQ/picnic area

4. Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG
2.5 star property
Sarasota
8.0 out of 10, Very Good, (1,010 reviews)
  • cleanliness
    Dive into refreshing bliss at this beachside haven with a sparkling outdoor pool and hot tub sanctuary.
$64 nightly
The price is $72
Sep 2 - Sep 3
Total with taxes and fees
Holiday Inn Express Sarasota East - I-75 by IHG
Outdoor pool, free cabanas, pool umbrellas

5. Turtle Beach Resort

Turtle Beach Resort
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (360 reviews)
  • cleanliness
    Private hot tubs and a serene outdoor pool await on this peaceful retreat near Turtle Beach.
$324 nightly
The price is $362
Aug 22 - Aug 23
Total with taxes and fees
Turtle Beach Resort
Outdoor pool, pool umbrellas, sun loungers

6. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
3.0 star property
Sarasota
8.4 out of 10, Very Good, (2,312 reviews)
  • cleanliness
    Splash into vacation mode with a sparkling poolside sanctuary just steps from Siesta Key Beach.
$98 nightly
The price is $110
Aug 30 - Aug 31
Total with taxes and fees
Spark by Hilton Sarasota Siesta Key Gateway
Outdoor pool

7. Carlisle Inn

Carlisle Inn
3.5 star property
Pinecraft
10.0 out of 10, Exceptional, (2,443 reviews)
  • cleanliness
    Refresh yourself poolside under the Florida sun in this tranquil Pinecraft sanctuary.
$152 nightly
The price is $172
Aug 5 - Aug 6
Total with taxes and fees
Carlisle Inn
Outdoor pool

8. Hampton Inn & Suites Venice Bayside South Sarasota

Hampton Inn & Suites Venice Bayside South Sarasota
2.5 star property
Gateway
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Sun-drenched relaxation awaits at this Venice hotel's outdoor pool, complemented by beach proximity and modern comforts.
$114 nightly
The price is $129
Aug 11 - Aug 12
Total with taxes and fees
Hampton Inn & Suites Venice Bayside South Sarasota
Property grounds

9. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,723 reviews)
  • cleanliness
    Sparkling private beachfront pool awaits just steps from your villa-style retreat.
$166 nightly
The price is $188
Aug 23 - Aug 24
Total with taxes and fees
Tropical Beach Resorts
Outdoor pool, a heated pool, sun loungers

10. Inn at the Beach

Inn at the Beach
3.0 star property
Venice Island
9.8 out of 10, Exceptional, (1,018 reviews)
  • cleanliness
    Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
$166 nightly
The price is $188
Aug 6 - Aug 7
Total with taxes and fees
Inn at the Beach
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

Top Osprey Hotel Reviews

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"I didnt know what to expect when I chose this place bc the price was great and Ive been fooled by online pictures before. And when I pulled up I was a little nervous. But my fears were immediately sudsided when I walked in and the first thing I noticed was how it looked recently updated and clean and then was greeted by a helpful informative and friendly desk attendant that worked w a sense of urgency. I found my parking spot quick and then my room and walked in and was flooded with a sense of relief when i realized the pictures matched the room. It too looked recently updated and clean. Also the rooms were quiet the hotel was full and I didnt hear anyone else. They also hooked me up w a free drink ticket so I walked over and checked out the Tiki Hut Bar. Once again I was greeted by friendly attentive and entertaining bartenders. They also have a pool and hot tub. And a working ice machine. Deff great value here for the price. Great job yall"
Josh 2-night trip
Posted 10 hours 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 $72 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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