Photo by Rick Tuers

Find Hotels with a Pool in Osprey, FL

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 a Pool

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, (1066)
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 ￥19,771
￥22,341 total
includes taxes & fees
Nov 30 - Dec 1
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, (4617)
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, 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, (1001)
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 ￥8,473
￥9,998 total
includes taxes & fees
Nov 13 - Nov 14
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, (342)
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.
The price is ￥15,560
￥17,583 total
includes taxes & fees
Nov 18 - Nov 19
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
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, (1002)
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.
The price is ￥15,033
￥16,988 total
includes taxes & fees
Nov 30 - Dec 1
Best Western Plus Ambassador Suites Venice
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, (1000)
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 ￥10,516
￥19,717 total
includes taxes & fees
Nov 18 - Nov 19
Siesta Key Palms Resort
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, (337)
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.
The price is ￥8,318
￥9,649 total
includes taxes & fees
Nov 16 - Nov 17
Motel 6 Venice, FL
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, (1012)
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.
Inn at the Beach
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, (584)
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 ￥17,748
￥20,054 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites North Port
Outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas, sun 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, (229)
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.
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

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Fantastic Stay! I had a wonderful experience at this hotel. The staff were friendly and welcoming, the room was spotless and comfortable, and every detail made the stay enjoyable. The location was convenient, and the amenities exceeded my expectations. I’d definitely stay here again and recommend it to anyone looking for a relaxing, high-quality stay!"
Robert 2-night trip
Posted 1 day ago
The Westin Sarasota

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. 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.