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Find Hotels with a Pool in Osprey, FL

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Top Osprey Hotels with a Pool

Outdoor dining
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 star property
Osprey
  • Outdoor pool
  • Poolside bar
  • Pool loungers
8.6 out of 10, Excellent, (1064)
Sparkling waters beckon in the immaculate outdoor pool area, where complimentary cabanas provide shade after beach adventures. Live entertainment creates a lively atmosphere while the nearby restaurant serves exceptional meals praised by guests.
$128 nightly
The price is $145
Nov 30 - Dec 1
Total with taxes and fees
Casey Key Resorts - Mainland
Outdoor pool, a heated pool
Kompose Boutique Hotel

Kompose Boutique Hotel

3.0 star property
Sarasota
  • Outdoor pool
  • Hot tub
9.2 out of 10, Wonderful, (4606)
Sparkling beneath the sun, the heated outdoor pool provides a refreshing escape after exploring nearby beaches. Guests particularly love unwinding in the hot tub before retiring to spotlessly clean, modern rooms with rainfall showers.
$83 nightly
The price is $94
Nov 16 - Nov 17
Total with taxes and fees
Kompose Boutique Hotel
Outdoor pool
Sun Coast Inn

Sun Coast Inn

2.5 star property
Englewood South
  • Outdoor pool
  • Near the beach
7.8 out of 10, Good, (853)
Refreshing swims await in the sun-drenched outdoor pool with beautiful canal views, just steps from Englewood Beach. Spacious, spotless rooms with premium bedding complement exceptional staff service, making this peaceful retreat an ideal coastal escape.
$83 nightly
The price is $93
Nov 11 - Nov 12
Total with taxes and fees
Sun Coast Inn
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
  • Outdoor pool
  • Pool loungers
  • Near the beach
7.6 out of 10, Good, (1000)
Poolside tranquility awaits at this well-maintained getaway near Venice Beach. Guests adore the clean, peaceful swimming area surrounded by a lovely courtyard. After exploring nearby attractions, unwind with convenient room service from the highly-rated on-site restaurant.
$58 nightly
The price is $65
Nov 12 - Nov 13
Total with taxes and fees
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
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
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.6 out of 10, Exceptional, (340)
Refreshing swims await in the sun-drenched outdoor pool, complete with comfortable loungers for relaxation after beach adventures. Guests appreciate the convenient location near beautiful shorelines, kayaking spots, and sailing opportunities.
$101 nightly
The price is $114
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
2 outdoor pools, a heated pool
Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 star property
Sarasota
  • 2 outdoor pools
  • Near the beach
9.2 out of 10, Wonderful, (1006)
Aquatic serenity awaits at this tropical haven where 2 refreshing outdoor pools anchor the experience. Complimentary bicycles invite exploration of nearby Siesta Key shores, while fire pits and hammocks create perfect relaxation spots after sun-soaked adventures.
$121 nightly
The price is $137
Nov 18 - Nov 19
Total with taxes and fees
Siesta Key Palms Resort
Outdoor pool, pool umbrellas, sun loungers
Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice

2.5 star property
Venice
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (1005)
Spacious poolside retreats with comfortable loungers and umbrellas create a refreshing outdoor oasis. Beyond crystal-clear waters, guests appreciate spotless accommodations, complimentary full breakfast, and exceptionally attentive staff.
$98 nightly
The price is $110
Nov 17 - Nov 18
Total with taxes and fees
Best Western Plus Ambassador Suites Venice
Outdoor pool, a heated pool, sun loungers
Inn at the Beach

Inn at the Beach

3.0 star property
Venice Island
  • Outdoor pool
  • Pool loungers
  • Near the beach
  • Hot tub
9.8 out of 10, Exceptional, (1006)
Sparkling pool waters beckon after a day exploring nearby Venice Beach. Relaxation continues in the clean hot tub while sunsets paint the sky. Continental breakfast, bicycle rentals, and barbecue areas complement this peaceful beachfront haven.
$166 nightly
The price is $188
Nov 17 - Nov 18
Total with taxes and fees
Inn at the Beach
Outdoor pool
Motel 6 Venice, FL

Motel 6 Venice, FL

2.0 star property
Gateway
  • Outdoor pool
  • Near the beach
8.4 out of 10, Very Good, (333)
Swimming enthusiasts relish the pristine outdoor pool, accessible daily from 8:00 AM to 9:00 PM. Beyond aquatic pleasures, this dog-friendly motel features charcoal grills, picnic areas, and easy access to Venice Beach for complete vacation satisfaction.
$56 nightly
The price is $63
Nov 16 - Nov 17
Total with taxes and fees
Motel 6 Venice, FL
Seasonal outdoor pool
Hampton Inn & Suites North Port

Hampton Inn & Suites North Port

2.5 star property
North Port
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Restaurant
  • Air conditioning
9.4 out of 10, Exceptional, (583)
Swimming enthusiasts appreciate the clean, beautiful seasonal outdoor pool at this modern hotel. Beyond aquatic enjoyment, guests rave about the amazing breakfast buffet, attentive staff, and peaceful atmosphere.
$121 nightly
The price is $136
Nov 24 - Nov 25
Total with taxes and fees
Hampton Inn & Suites North Port
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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Top Osprey Hotel Reviews

Comfort Suites Sarasota - Siesta Key

Comfort Suites Sarasota - Siesta Key

10/10 Excellent
"Staff was very courteous & helpful. Clean room, bathtub needs updated."
Theresa 1-night trip
Posted 1 day ago
Comfort Suites Sarasota - Siesta Key

Frequently asked questions

What are some hotels with pools in Osprey?
Casey Key Resorts - Mainland: Features a snack bar/deli, an outdoor pool, and free self parking. Kompose Boutique Hotel: Offers a snack bar/deli, a pool, and complimentary wireless internet access. Tropical Beach Resorts: Aparthotel, 9-minute walk from Crescent Beach. Provides free self parking, an outdoor pool, and complimentary wireless internet access. Spark by Hilton Sarasota Siesta Key Gateway: Hotel located near Siesta Key Beach. Features daily, an outdoor pool, and free self parking. Tropical Breeze Resort: Hotel, 3-minute walk from Siesta Key Beach. Offers free self parking, 2 outdoor pools, and complimentary bicycles.
What is there to see and do in Osprey?
Explore places like Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions like Turtle Beach and Nokomis Beach. Osprey appeals to visitors with its beautiful beaches, bar scene, and array of dining options.
When is the best time to book a hotel with a pool in Osprey?
Taking into account the local weather in Osprey can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Osprey is 44 inches.

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