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

Hotels with Swimming Pool in Summerland Key, Florida

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Check availability on Summerland Key Hotels with Swimming Pool

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and the ocean.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

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.
P8,446
P11,556 total
includes taxes & fees
Nov 2 - Nov 3
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
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.
P7,495
P8,432 total
includes taxes & fees
Oct 26 - Oct 27
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 spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
P8,832
P9,936 total
includes taxes & fees
Oct 26 - Oct 27
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 two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

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.
P32,592
P61,465 total
includes taxes & fees
Oct 20 - Oct 21
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 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.
A floating houseboat with a covered deck and seating area, docked at a marina.

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 onsite marina and private dock.
P5,612
P15,170 total
includes taxes & fees
Oct 20 - Oct 21
Old Wooden Bridge Resort and Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
Breakfast area
A hotel room with a balcony, a bed, a desk, and two chairs.
A balcony with wicker furniture and a view of the ocean and palm trees.

6. 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.
P10,644
P11,974 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A waterfront hotel with a pool, palm trees, and a wooden dock.
A clear view of turquoise ocean water and a blue sky with clouds.
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.

7. 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.
P7,695
P12,341 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Key West Resort & Marina
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

8. 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.
P8,446
P11,272 total
includes taxes & fees
Oct 26 - Oct 27
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
An aerial view of a resort with a central pool, multiple buildings, and a beach area with sun loungers.
A beach scene with two white chairs, a hammock, and palm trees.
A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.
A beach with white chairs and kayaks, palm trees, and a clear view of the ocean.

9. Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
Marathon
  • Sun-kissed island retreat offers five heated pools with loungers and poolside cocktails.
P11,280
P16,400 total
includes taxes & fees
Oct 20 - Oct 21
Isla Bella Beach Resort & Spa
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A person standing by a window overlooking a beach with palm trees and the ocean.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
A beach with a palm tree and two chairs.

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.
P13,163
P18,782 total
includes taxes & fees
Oct 20 - Oct 21
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

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
Mariia 1-night trip
Posted 1 day ago
Sugar Loaf Lodge
Parmer's Resort

Parmer's Resort

10/10 Excellent
"I've stayed at Parmers several times and anytime I'm in the Keys Parmers is where I stay. Staff is excellent."
Ken 2-night trip
Posted 4 days ago
Parmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"They had a nice pool you could park your boat in the channel they also had a very nice tiki bar and grill it was an ok place to stay but parking sucked"
Todd c 1-night trip
Posted 8 days ago
Looe Key Reef Resort

Frequently asked questions

What's it like visiting Summerland Key?
If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that travelers like for their pools.
What are some accommodations 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 will I be able 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 like 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 into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Summerland Key is 35 inches.

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