A coastal road with a beach on one side and a marina with boats on the other.

Search Hotels with Swimming Pool in Summerland Key

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Check availability on Summerland Key Hotels with Swimming Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Summerland Key hotels with a pool

A sunset view with a thatched structure and a palm tree by a calm body of water.
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

1. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
₹12,198
₹16,865 total
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
₹11,461
₹12,894 total
includes taxes & fees
6 Oct - 7 Oct
Sugar Loaf Lodge
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
₹9,717
₹10,931 total
includes taxes & fees
7 Oct - 8 Oct
Looe Key Reef Resort
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A bedroom with a bed, a ceiling fan, a balcony with a view, and a nightstand with a lamp.
A two-story building with a balcony, surrounded by tropical vegetation.
A concrete pathway flanked by lush green foliage, leading to a shaded area.

4. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
  • Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days.
₹49,840
₹93,991 total
includes taxes & fees
9 Oct - 10 Oct
Atlantic View Luxury Villa with Pool
A fenced pool area with palm trees, a blue and white tiled walkway, and a sign indicating pool hours.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.

5. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
Punta Brisa
  • Soak in tropical views at the outdoor pool, then paddle away from this waterfront cottage with an on-site marina and private dock.
₹12,915
₹28,073 total
includes taxes & fees
6 Oct - 7 Oct
Old Wooden Bridge Resort and Marina
A waterfront hotel with a pool, palm trees, and a wooden dock.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.
A marina with numerous boats docked, a swimming pool, and palm trees.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

6. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.
₹12,162
₹19,316 total
includes taxes & fees
12 Oct - 13 Oct
Hilton Key West Resort & Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a balcony, a bed, a desk, and two chairs.
View from room
Breakfast area

7. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
₹16,276
₹18,311 total
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn Key West FL
An aerial view of a resort with a central pool, multiple buildings, and a beach area with sun loungers.
Room
A beach scene with two white chairs, a hammock, and palm trees.
A beach with white chairs and kayaks, palm trees, and a clear view of the ocean.

8. Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
Marathon
  • Sun-kissed island retreat offers five heated pools with loungers and poolside cocktails.
₹22,450
₹31,106 total
includes taxes & fees
6 Oct - 7 Oct
Isla Bella Beach Resort & Spa
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A modern office space with a reception desk, computer, and seating area.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

9. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
  • Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.
₹12,915
₹17,238 total
includes taxes & fees
11 Oct - 12 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A beach with a palm tree and two chairs.
A person standing by a window overlooking a beach with palm trees and the ocean.

10. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
  • Float in serene waters at this sun-soaked poolside paradise with direct beach access and friendly round-the-clock service.
₹20,129
₹28,722 total
includes taxes & fees
6 Oct - 7 Oct
Margaritaville Beach House Key West
View all properties

Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Summerland Key Hotel Reviews

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"The room was super clean. The fact that we can keep a boat docked right behind our room is amazing. There is a tiki bar literally right in front of the room is a plus. Check out was easy and quick as well as check in. I mean best decision ever."
anneliss 2-night trip
Posted 1 day ago
Looe Key Reef Resort
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Just a fantastic property, wonderful staff, great amenities, so many waterfront places to chill. Immaculate grounds with a laid back vibe, loved it!!"
Moira 1-night trip
Posted 1 day ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
Richard 2-night trip
Posted 10 days ago
Sugar Loaf Lodge

Frequently asked questions

What's it like visiting Summerland Key?
If taking it easy by the pool is your idea of a great getaway, you may want to look at Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions such as Florida Keys Beaches, and then relax and unwind poolside at one of the accommodation options in Summerland Key that travellers like for their pools.
What are some accommodation options with pools in Summerland Key?
Parmer's Resort: Features a private beach, an outdoor pool and daily. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool and a snack bar/deli. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool and a full-service spa. Looe Key Reef Resort: Features free self parking, an outdoor pool and complimentary wireless Internet access. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Offers free self parking, an outdoor pool and complimentary wireless Internet access.
How many hotels with pools can I expect to find in Summerland Key?
Expedia's 27 hotels in Summerland Key give you a great choice for your poolside getaway.
What is there to see and do in Summerland Key?
Explore places such as Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Venture Out Keys.
When is the best time to book a hotel with a pool in Summerland Key?
Taking the local weather in Summerland Key into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Summerland Key is 895 mm.

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