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

Sugarloaf Key Hotel Guide - Hotels with Pool in Sugarloaf Key, Summerland Key

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Check availability on Sugarloaf Key Hotels with Pool

Tonight
4 Sept - 5 Sept
Tomorrow
5 Sept - 6 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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 waterfront building with a flat roof, large windows, and a balcony.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
€98
includes taxes & fees
7 Sept - 8 Sept
Sugar Loaf Lodge
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 thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
€73
includes taxes & fees
7 Sept - 8 Sept
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 marina with numerous boats docked, a swimming pool, and palm trees.
A clear view of turquoise ocean water and a blue sky with clouds.

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.
€162
includes taxes & fees
17 Sept - 18 Sept
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 spacious living area with a wooden ceiling, a ceiling fan, a TV, a glass coffee table, a sofa, a chair, and a kitchen area with a refrigerator and bar stools.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€349
includes taxes & fees
9 Sept - 10 Sept
SAVE BIG $$$ 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 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 white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

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.
€191
includes taxes & fees
20 Sept - 21 Sept
Parmer's Resort
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 floating houseboat with a covered deck and seating area, docked at a marina.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.

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 on-site marina and private dock.
€208
includes taxes & fees
7 Sept - 8 Sept
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.
A balcony with wicker furniture and a view of the ocean and palm trees.

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.
€134
includes taxes & fees
22 Sept - 23 Sept
Hampton Inn Key West FL
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A balcony with wicker furniture, a red chair, and a lamp.
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.

8. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
€175
includes taxes & fees
15 Sept - 16 Sept
Beachside Resort & Residences
A swimming pool with blue and white tiled edges, surrounded by palm trees and white lounge chairs.
A stone sculpture with a face, surrounded by rocks and palm trees.
A balcony with white chairs and a table, overlooking a pool and a marina with boats.
A kitchen with white cabinets, a microwave, a stove, a sink, and a refrigerator.

9. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
€324
includes taxes & fees
10 Sept - 11 Sept
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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
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.
€155
includes taxes & fees
9 Sept - 10 Sept
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 8 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 11 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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