A waterfront with a pier, calm water, and houses with palm trees in the background.

Find Hotels with a Pool in Sugarloaf Key, FL

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Check availability on Sugarloaf Key Hotels with a Pool

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Sugarloaf Key hotels with a pool

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.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
$119 nightly
$134 total
Oct 26 - Oct 27
Total with taxes and fees
Sugar Loaf Lodge
A waterfront hotel with a pool, palm trees, and a wooden dock.
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.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.

2. 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.
$169 nightly
$190 total
Oct 26 - Oct 27
Total with taxes and fees
Hilton Key West Resort & Marina
A large swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
Sports facility
A modern living room with a sectional sofa, a small round table, and a potted plant.

3. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.
$135 nightly
$151 total
Oct 29 - Oct 30
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A balcony with wicker furniture and a view of the ocean and palm trees.
View from room
Breakfast area

4. 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.
$149 nightly
$168 total
Oct 25 - Oct 26
Total with taxes and fees
Hampton Inn Key West FL
A sunset view with a thatched structure and a palm tree by a calm body of water.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
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.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

5. 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.
$178 nightly
$200 total
Nov 1 - Nov 2
Total with taxes and fees
Parmer's Resort
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
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 wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

6. 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.
$135 nightly
$151 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

7. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$140 nightly
$158 total
Nov 10 - Nov 11
Total with taxes and fees
Looe Key Reef Resort
A hotel with a swimming pool surrounded by palm trees and blue lounge chairs.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
  • Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.
$148 nightly
$166 total
Oct 28 - Oct 29
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A couple holding hands in a tropical setting with palm trees and greenery.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

9. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
  • Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
$166 nightly
$187 total
Oct 25 - Oct 26
Total with taxes and fees
Blue Flamingo Resort Key West
A fenced pool area with palm trees, a blue and white tiled walkway, and a sign indicating pool hours.
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.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

10. 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.
$222 nightly
$250 total
Oct 25 - Oct 26
Total with taxes and fees
Old Wooden Bridge Resort and Marina
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Choose what matters most at hotels with a pool in Sugarloaf Key

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Sugarloaf Key Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"Close to Duval Street"
Gregory 1-night trip
Posted 14 hours ago
The Southernmost Inn - Adults Only
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Not our first stay but it’s always a pleasure staying there. We have nothing bad to say after 4 stays over the years"
Joseph 3-night trip
Posted 2 days ago
DoubleTree Resort by Hilton Grand Key - Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still waiting on the itemized bill, believe we were overcharged on “extras”."
Lisa 2-night trip
Posted 4 days ago
Hilton Garden Inn Key West / The Keys Collection

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