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

Find Hotels with Pool in Sugarloaf Key, FL

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Check availability on Sugarloaf Key Hotels with Pool

Tonight
21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Sugarloaf Key hotels with a pool

A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.
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.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
£83
includes taxes & fees
27 Sept - 28 Sept
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 thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
£64
includes taxes & fees
23 Sept - 24 Sept
Looe Key Reef Resort
A poolside area with lounge chairs and a view of boats in the background.
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 hotel room with a balcony overlooking a marina and the ocean.

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.
£133
includes taxes & fees
28 Sept - 29 Sept
Hilton Key West Resort & Marina
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A waterfront property with a two-story building, a covered outdoor area, and a dock.
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
A balcony with a view of neighboring houses, a street, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
£293
includes taxes & fees
27 Sept - 28 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 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.
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.
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.
£145
includes taxes & fees
4 Oct - 5 Oct
Parmer's Resort
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.

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.
£114
includes taxes & fees
27 Sept - 28 Sept
Hampton Inn Key West FL
A marina with boats, a dock, and a white building with a balcony.
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.
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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
£302
includes taxes & fees
22 Sept - 23 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 sea, and a spiral staircase.
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.
£145
includes taxes & fees
22 Sept - 23 Sept
Beachside Resort & Residences
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 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.

9. 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.
£181
includes taxes & fees
27 Sept - 28 Sept
Old Wooden Bridge Resort and Marina
A swimming pool surrounded by palm trees and a natural rock formation.
A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.
A spacious lobby with a central seating area, two staircases, and multiple potted plants.
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

10. Havana Cabana at Key West

Havana Cabana at Key West
New Town
  • Poolside paradise awaits with hot tub, dining, and bar service at this vibrant Key West oasis.
£140
includes taxes & fees
27 Sept - 28 Sept
Havana Cabana at 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

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Me encantó la verdad muy limpio trankilo y para ir en familia y con niños lo recomiendo mucho gracias"
Suany 2-night trip
Posted 1 hour ago
Hampton Inn Key West FL
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Comfortable beds"
Paul 3-night trip
Posted 2 hours ago
Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"A little annoyed at the gate that got locked (leading us to our room), and that the gate was not repaired during our stay, but that was the only real issue out of the entire stay."
Nicholas James 6-night trip
Posted 4 hours ago
Southernmost Beach Resort and Guesthouses
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good
"Love the balcony setting, the rooms layout as well as the ocean view"
John 3-night trip
Posted 5 hours ago
Hyatt Vacation Club at Windward Pointe, Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 5 hours ago
Ibis Bay Beach Resort
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"This was our second time staying at The Perry and this time we brought friends. The location on the marina is really nice and there are restaurants nearby, like Roostica! We did notice from our 1st stay that the rooms are needing a little TLC regarding maintenance and repairs. Nothing serious, just an observation. BONUS they have an hourly shuttle to/from Key West! We will stay here again!"
Jamie 1-night trip
Posted 5 hours ago
The Perry Hotel & Marina Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Was a great place beds could use a little upgrade"
Joseph 4-night trip
Posted 1 day ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"The hotel was clean, great customer service, and the food was really good!"
Craige 3-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West

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