Hotels with Swimming Pools in Osprey

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Osprey Hotels with Swimming Pools

Top Hotels with Swimming Pools in Osprey

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, (1072)
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.
The price is S$189
includes taxes & fees
30 Nov - 1 Dec
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, (4648)
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.
Kompose Boutique Hotel
Outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas, pool 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, (1003)
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.
The price is S$85
includes taxes & fees
19 Nov - 20 Nov
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
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, (1001)
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.
The price is S$156
includes taxes & fees
2 Dec - 3 Dec
Siesta Key Palms Resort
Outdoor pool, a heated pool, pool 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.
The price is S$218
includes taxes & fees
2 Dec - 3 Dec
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, (343)
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 holiday satisfaction.
The price is S$91
includes taxes & fees
23 Nov - 24 Nov
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, (587)
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.
The price is S$174
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn & Suites North Port
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, (857)
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.
The price is S$121
includes taxes & fees
19 Nov - 20 Nov
Sun Coast Inn
Outdoor pool, pool umbrellas, pool 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, (1000)
Spacious poolside retreats with comfortable loungers and umbrellas create a refreshing outdoor oasis. Beyond crystal-clear waters, guests appreciate spotless accommodation, complimentary full breakfast, and exceptionally attentive staff.
The price is S$150
includes taxes & fees
26 Nov - 27 Nov
Best Western Plus Ambassador Suites Venice
Outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas, pool loungers
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 star property
Casey Key
  • Outdoor pool
  • Pool loungers
  • Near the beach
9.8 out of 10, Exceptional, (230)
Sparkling blue waters await in the meticulously maintained outdoor pool, complemented by comfortable loungers for ultimate relaxation. Nearby hot springs provide therapeutic soaking options, while the marina and beach access create a complete coastal experience.
The price is S$190
includes taxes & fees
19 Nov - 20 Nov
Escape Coastal Resort on Casey Key
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.
View all properties

Top Osprey Hotel Reviews

Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"Great atmosphere and excellent amenities "
Matthew 1-night trip
Posted 4 days ago
Siesta Key Palms Resort

Explore a world of travel with Expedia

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. Tropical Breeze Resort: Hotel, 3-minute walk from Siesta Key Beach. Features free self parking, 2 outdoor swimming pools and complimentary bicycles. Spark by Hilton Sarasota Siesta Key Gateway: Hotel located near Siesta Key Beach. Offers daily, an outdoor pool and free self parking.
What is there to see and do in Osprey?
Explore places such as Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions such as 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 the local weather in Osprey into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 19°C. Average annual precipitation for Osprey is 1126 mm.