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 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
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 waterfront building with a flat roof, large windows, and a balcony.
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.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
￥18,835
￥21,190 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
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 marina with RVs docked along a waterway, surrounded by palm trees and buildings.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
￥29,915
￥76,133 total
includes taxes & fees
Oct 25 - Oct 26
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
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.

3. 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.
￥18,376
￥25,125 total
includes taxes & fees
Oct 28 - Oct 29
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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.
View from room

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.
￥26,749
￥30,093 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A beach view with a swimming pool, palm trees, and lounge chairs.
A waterfront property with a pool, palm trees, and a house with a balcony.
A spacious living room with a white sofa, two armchairs, a round coffee table, and a balcony with a view of palm trees.
A two-story house with a balcony, a staircase, and a view of the beach.

5. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
￥51,441
￥114,576 total
includes taxes & fees
Oct 22 - Oct 23
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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 hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.
A clear view of turquoise ocean water and a blue sky with clouds.

6. 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.
￥18,690
￥30,285 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Key West Resort & Marina
A resort with a swimming pool, beach area, and marina.
A waterfront property with a boat dock, a covered outdoor seating area, and a two-story building with balconies.
A spacious living room with a large TV, comfortable seating, a wooden cabinet, and a view of the sea through large windows.
A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

7. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
￥62,279
￥118,722 total
includes taxes & fees
Oct 25 - Oct 26
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.
A modern hotel room with a balcony, a grey sofa, a red chair, a white coffee table, and a painting of a tropical scene.

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.
￥16,968
￥24,432 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
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.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
￥25,167
￥70,791 total
includes taxes & fees
Oct 22 - Oct 23
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
A multi-story hotel with balconies, palm trees, and a pool area.

10. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
  • Dive into aquatic bliss with two poolside bars and waterfront dining at this Key West retreat.
￥15,173
￥26,328 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina 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

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"N/A"
Richard 3-night trip
Posted 3 hours ago
Opal Key Resort & Marina, Key West
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"Room smelled a little moldy/musty but otherwise great"
Joseph 2-night trip
Posted 3 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"All I can say is all aspects were fantastic"
Joseph 3-night trip
Posted 5 hours ago
Casa Marina Key West, Curio Collection by Hilton
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 5 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"You can't beat the location. It is easy to get to and around the area. I like being close to the beach and there is places to eat at on the property. I would stay here again. The rooms are clean but average. It was all we needed though. I was happy with the hotel pic."
Robin 2-night trip
Posted 7 hours ago
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"great room, pool, laundry, tiki bar, staff"
Pamela 5-night trip
Posted 8 hours ago
Beachside Resort & Residences
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 2 days ago
Hilton Garden Inn Key West / The Keys Collection

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