A marina with docked boats, a wooden bridge, and a building with a red roof.

Find Hotels with a Pool in Osprey, FL from CA $99

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Check availability on Osprey Hotels with a Pool

Tonight
Aug 19 - Aug 20
Tomorrow
Aug 20 - Aug 21
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Osprey hotels with a pool

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.
CA $124
CA $157 total
includes taxes & fees
Aug 21 - Aug 22
Casey Key Resorts - Mainland

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.
CA $129
CA $146 total
includes taxes & fees
Sep 13 - Sep 14
Comfort Suites Sarasota - Siesta Key

3. 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.
CA $117
CA $132 total
includes taxes & fees
Sep 16 - Sep 17
Holiday Inn Express Sarasota East - I-75 by IHG

4. 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.
CA $135
CA $153 total
includes taxes & fees
Sep 3 - Sep 4
Spark by Hilton Sarasota Siesta Key Gateway

5. Tropical Beach Resorts

Tropical Beach Resorts
South Village
  • Sparkling private beachfront pool awaits just steps from your villa-style retreat.
CA $177
CA $236 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts

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.
CA $105
CA $190 total
includes taxes & fees
Aug 20 - Aug 21
Siesta Key Palms Resort

7. Inn at the Beach

Inn at the Beach
Venice Island
  • Sparkling beachfront pool invites evening dips with stunning sunset views across the water.
CA $143
CA $198 total
includes taxes & fees
Sep 7 - Sep 8
Inn at the Beach

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.
CA $92
CA $104 total
includes taxes & fees
Aug 23 - Aug 24
Days Inn by Wyndham Sarasota I-75

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.
CA $158
CA $179 total
includes taxes & fees
Aug 26 - Aug 27
Hampton Inn & Suites Venice Bayside South Sarasota

10. 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.
CA $166
CA $274 total
includes taxes & fees
Sep 7 - Sep 8
Escape Coastal Resort on Casey Key
View all properties

Choose what matters most at hotels with a pool in Osprey

Breakfast included
Hot tub
4 stars
5 stars
Beach

Top Osprey Hotel Reviews

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Beautiful 10/10 recommend 👌"
Adrian 2-night trip
Posted 14 hours ago
Siesta Key Beach Resort and Suites
Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Very clean and amazing amenities. Gorgeous pool and access to the beach"
Sheila 2-night trip
Posted 18 hours ago
Zota Beach Resort
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Clean facility friendly staff easy check-in and check out."
Melissa 3-night trip
Posted 20 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"😊 👍👍 good"
Cesar 1-night trip
Posted 21 hours ago
Casey Key Resorts - Mainland
The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Great location. Very walkable to marina and downtown. Awesome view from rooftop bar. Nice pool and pool deck on rooftop as well. Great staff. 2nd stay here."
Steve 1-night trip
Posted 22 hours ago
The Westin Sarasota

Frequently asked questions

What are the best hotels in Osprey with outdoor pools?
Casey Key Resorts - Mainland is a fantastic choice for travellers seeking a relaxing getaway in Osprey, Florida. This hotel features an inviting outdoor pool, complete with poolside cabanas and sun loungers, great for soaking up the sun with your family. Guests consistently rave about the friendly and amazing staff, ensuring an inviting space for all.With a traveller rating of 8.6, Casey Key Resorts is not just about the pool; the spacious and clean rooms provide a comfortable retreat after a day of adventures. The hotel's location is praised for its accessibility to nearby attractions, making it a convenient base for exploring the beautiful Gulf Coast. Plus, the excellent dining options make it easy to enjoy delicious meals without venturing far from your cozy accommodations.
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 CA $99 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 a fantastic option for travellers seeking a relaxing getaway in Osprey, Florida. This charming hotel features a delightful outdoor pool area, complete with complimentary pool cabanas and sun loungers, making it an ideal spot for soaking up the sun or enjoying a leisurely afternoon with family.Guests rave about the friendly and accommodating staff, who go above and beyond to ensure a pleasant stay. The clean, spacious rooms provide a comfortable retreat after a day of adventure, and the on-site poolside bar offers refreshing drinks to enjoy while lounging by the water. With a review rating of 8.6, travellers appreciate the excellent food options and the hotel's prime location, which enhances the overall experience.
Which Osprey hotels offer poolside service for food and drinks?
Casey Key Resorts - Mainland is a delightful option for travellers seeking a refreshing getaway in Osprey, Florida. With a well-rated score of 8.6, this hotel stands out for its inviting outdoor pool and vibrant poolside bar, where guests can enjoy a selection of food and drinks without leaving their sun lounger.Families will appreciate the spacious rooms, which are not only clean but also designed for comfort, making it an ideal retreat after a day of adventure. The friendly and attentive staff further enhances the experience, ensuring that your stay is both enjoyable and relaxing.
Are there hotels with outdoor pools that are close to Nokomis Beach?
Casey Key Resorts - Mainland is a fantastic option for travellers seeking a hotel with an outdoor pool close to Nokomis Beach. Rated 8.6 by guests, this resort is celebrated for its friendly and attentive staff, ensuring an inviting space from the moment you arrive.What truly sets this resort apart is its inviting outdoor pool area, complete with poolside cabanas and sun loungers, superb for relaxing after a fun day at the beach. Guests rave about the cleanliness and spaciousness of the rooms, along with the excellent food offerings available on-site, making it a convenient choice for families looking to balance adventure and comfort.In addition to its appealing amenities, Casey Key Resorts - Mainland boasts a prime location that allows for easy access to the beautiful shores of Nokomis Beach, making it an ideal base for both relaxation and outdoor activities.
Are there hotels in Osprey with outdoor pool activities or events?
Osprey, Florida, is a delightful destination that combines the charm of coastal living with a wealth of outdoor activities. For those seeking a refreshing dip, you'll find several hotels in the area featuring outdoor pools, making it an ideal spot for relaxation and family fun.Gilmore Resorts, which includes both Driftwood Lodge and Osprey on the Gulf, stands out with its heated pools adjacent to the stunning Gulf of Mexico. Here, families can enjoy barbecue stations, beachfront volleyball, and a splash pad that delights children. The planned events foster a vibrant, family-friendly atmosphere, ensuring everyone has a memorable time.For those travelling with families, Casey Key Resorts is another excellent choice. This hotel boasts an outdoor heated pool and a poolside bar, creating a laid-back environment where parents can unwind while kids splash about. With amenities like banquet rooms for hosting events, families can easily plan gatherings or celebrations during their stay.Moreover, you'll discover other hotels in Osprey that advertise outdoor pools, some heated, complete with poolside bars and outdoor dining options. This variety promises an array of opportunities for leisurely afternoons spent by the water, mingling with fellow guests, and enjoying the beautiful Florida sunshine.
Is it cheaper to book flights and a hotel in Osprey 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 travel 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 with an outdoor pool in Osprey for you.
How can I save on a hotel in Osprey 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 instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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