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 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 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.
$99 nightly
$111 total
Sep 27 - Sep 28
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 sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
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 snorkeling adventures nearby.
$92 nightly
$104 total
Sep 27 - Sep 28
Total with taxes and fees
Looe Key Reef 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 floating houseboat with a covered deck and seating area, docked at a marina.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

3. 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 27 - Sep 28
Total with taxes and fees
Old Wooden Bridge Resort and Marina
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 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 spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

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.
$173 nightly
$194 total
Oct 4 - Oct 5
Total with taxes and fees
Parmer's Resort
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 marina with RVs docked along a waterway, surrounded by palm trees and buildings.
A balcony with a view of neighboring houses, a street, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$351 nightly
$392 total
Sep 27 - Sep 28
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A poolside area with lounge chairs and a view of boats in the background.
A hotel room with a balcony overlooking a marina and the ocean.
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.

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.
$159 nightly
$179 total
Sep 30 - Oct 1
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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$373 nightly
$416 total
Sep 28 - Sep 29
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. 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 multi-story hotel with balconies, palm trees, and a pool area.
A modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

8. 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.
$184 nightly
$207 total
Sep 24 - Sep 25
Total with taxes and fees
The Perry Hotel & Marina Key West
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.

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.
$113 nightly
$180 total
Sep 28 - Sep 29
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 sea, and a spiral staircase.
A balcony with wicker furniture, a red chair, and a lamp.

10. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$185 nightly
$208 total
Sep 27 - Sep 28
Total with taxes and fees
Beachside Resort & Residences
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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

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"Nice, spacious rooms. Nice Pool and fantastic bar tender! Maintenance speedy if needed. Nice to have the shuttle to/from downtown. Enjoyed our stay very much."
Karen 4-night trip
Posted 9 hours ago
Beachside Resort & Residences
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Beautiful ambiance."
charles 2-night trip
Posted 9 hours ago
Casa Marina Key West, Curio Collection by Hilton
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Friendly and helpful staff. Love the 2 pools. It's great that they have a complimentary shuttle to take you downtown."
Melissa 1-night trip
Posted 9 hours ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Tyrone was extremely helpful with any need that came up. Even when it was not his responsibility, he made sure we were taken care of"
Benjamin Neil 3-night trip
Posted 11 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 2 days 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 2 days ago
The Perry Hotel & Marina Key West

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