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 corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.
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.
$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 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 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.
$170 nightly
$191 total
Oct 28 - Oct 29
Total with taxes and fees
Hilton Key West Resort & Marina
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A balcony with a view of neighboring houses, a street, and a clear sky.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.
A waterfront property with a two-story building, a covered outdoor area, and a dock.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$391 nightly
$434 total
Oct 22 - Oct 23
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. 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.
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.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

4. 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 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 sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

5. 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
Oct 26 - Oct 27
Total with taxes and fees
Looe Key Reef Resort
A large swimming pool with lounge chairs and palm trees.
Sports facility
A modern living room with a sectional sofa, a small round table, and a potted plant.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

6. 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.
$130 nightly
$147 total
Oct 28 - Oct 29
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
A balcony with a view of a pool area, palm trees, and outdoor seating.
A hotel room with a sofa, a small table, a lamp, and a balcony with 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.

7. 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.
$137 nightly
$154 total
Oct 29 - Oct 30
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A marina with boats, a dock, and a white building with a balcony.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$403 nightly
$447 total
Oct 22 - Oct 23
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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.
Breakfast area
View from room

9. 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.
$169 nightly
$190 total
Oct 25 - Oct 26
Total with taxes and fees
Hampton Inn Key West FL
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 modern office space with a reception desk, computer, and seating area.

10. 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.
$141 nightly
$159 total
Oct 28 - Oct 29
Total with taxes and fees
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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

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 1 hour 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 2 hours ago
Beachside Resort & Residences
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"We had no issues. Room clean, restaurant good!"
Michael 4-night trip
Posted 1 day 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

10/10 Excellent
"Wonderful hotel"
Jacob 1-night trip
Posted 1 day ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Limpio .buena atención. Transporte rápido para el centro y playa parqueo incluido para muchos carros"
rene 2-night trip
Posted 2 days ago
DoubleTree Resort by Hilton Grand Key - Key West

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