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
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Sugarloaf Key hotels with a pool

A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A waterfront building with a flat roof, large windows, and a balcony.
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
Sep 7 - Sep 8
Total with taxes and fees
Sugar Loaf Lodge
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
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.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$75 nightly
$84 total
Sep 7 - Sep 8
Total with taxes and fees
Looe Key Reef Resort
A poolside area with lounge chairs and a view of boats in the background.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
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.

3. 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.
$167 nightly
$188 total
Sep 16 - Sep 17
Total with taxes and fees
Hilton Key West Resort & Marina
A marina with boats, a dock, and a white building with a balcony.
A waterfront property with a covered porch, a boat dock, and a clear sky.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

4. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$365 nightly
$406 total
Sep 8 - Sep 9
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and the ocean.

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.
$198 nightly
$223 total
Sep 7 - Sep 8
Total with taxes and fees
Parmer's Resort
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 cozy room with a brown leather sofa, a white table, and a ceiling fan.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

6. 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.
$225 nightly
$253 total
Sep 7 - Sep 8
Total with taxes and fees
Old Wooden Bridge Resort and 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.

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.
$139 nightly
$156 total
Sep 20 - Sep 21
Total with taxes and fees
Hampton Inn Key West FL
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A beach view with a wooden pier, palm trees, and a sunset over the water.
A balcony with wicker furniture, a view of the water, and a railing.
A balcony with wicker furniture, a red chair, and a lamp.

8. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$195 nightly
$219 total
Sep 7 - Sep 8
Total with taxes and fees
Beachside Resort & Residences
A swimming pool with blue and white tiled edges, surrounded by palm trees and white lounge chairs.
A kitchen with white cabinets, a microwave, a stove, a sink, and a refrigerator.
A white building with large windows and a balcony, featuring outdoor furniture and a covered area.
A stone sculpture with a face, surrounded by rocks and palm trees.

9. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
$341 nightly
$379 total
Sep 9 - Sep 10
Total with taxes and fees
Canal Front home with easy Ocean access
A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A couple holding hands in a tropical setting with palm trees and greenery.

10. 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.
$160 nightly
$180 total
Sep 7 - Sep 8
Total with taxes and fees
Blue Flamingo Resort Key West
View all properties

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

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Clean room"
Luis 2-night trip
Posted 3 hours ago
Casa Marina Key West, Curio Collection by Hilton
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Very happy with our stay!"
David 2-night trip
Posted 4 hours ago
Parrot Key Hotel & Villas
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Greater beach hotel just outside the main strip but very easy uber ride Hotel right on a small beach great pool and seafood restaurant and small zoo for the children too"
Stephen 2-night trip
Posted 7 hours ago
Ibis Bay Beach Resort
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"Staff was very helpful and nice"
Cheri 5-night trip
Posted 9 hours ago
The Reach Key West, Curio Collection by Hilton
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Nice property. Very pleasant stay."
Cynthia 1-night trip
Posted 10 hours ago
Hampton Inn Key West FL
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location. Staff were very nice. Room clean. Food good."
David 5-night trip
Posted 20 hours ago
Pier House Resort & Spa
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Nice"
Kenneth 1-night trip
Posted 1 day ago
Hilton Garden Inn Key West / The Keys Collection
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"The staff were outstanding, especially Anna at the front desk. They all were so warm and welcoming. The rooms were spacious and clean. The pool was clean and mostly quiet (which was nice and relaxing)."
sharon 3-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."
Quantona 3-night trip
Posted 4 days ago
DoubleTree Resort by Hilton Grand Key - Key West

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