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

Search Hotels with Swimming Pool in Sugarloaf Key

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Check availability on Sugarloaf Key Hotels with Swimming Pool

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 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.
₹11,296
₹12,709 total
includes taxes & fees
26 Oct - 27 Oct
Sugar Loaf Lodge
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
View from room
Breakfast area
A hotel room with a balcony, a bed, a desk, and two chairs.

2. 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.
₹16,043
₹18,048 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A concrete pathway flanked by lush green foliage, leading to a shaded area.
A bedroom with a bed, a ceiling fan, a balcony with a view, and a nightstand with a lamp.
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

3. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
  • Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days.
₹49,124
₹92,642 total
includes taxes & fees
26 Oct - 27 Oct
Atlantic View Luxury Villa with Pool
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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

4. 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.
₹11,021
₹15,068 total
includes taxes & fees
28 Oct - 29 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
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.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

5. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
₹13,312
₹14,977 total
includes taxes & fees
26 Oct - 27 Oct
Looe Key Reef Resort
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 spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

6. 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.
₹12,392
₹17,038 total
includes taxes & fees
15 Nov - 16 Nov
Parmer's Resort
A waterfront hotel with a pool, palm trees, and a wooden dock.
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 hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.

7. 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.
₹11,209
₹18,163 total
includes taxes & fees
28 Oct - 29 Oct
Hilton Key West Resort & Marina
A balcony with a view of a pool area, palm trees, and outdoor seating.
A modern hotel room with a balcony, a grey sofa, a red chair, a white coffee table, and a painting of a tropical scene.
A hotel room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.
A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

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.
₹10,176
₹14,652 total
includes taxes & fees
29 Oct - 30 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A modern living room with a flat-screen TV, wooden cabinet, grey sofa, and a coffee table.
A marina with boats docked, a swimming pool, and palm trees.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

9. 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.
₹9,100
₹15,791 total
includes taxes & fees
16 Nov - 17 Nov
The Perry Hotel & Marina Key West
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.
A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

10. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
  • Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
₹17,488
₹23,946 total
includes taxes & fees
29 Oct - 30 Oct
Hyatt Vacation Club at Windward Pointe, Key West
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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

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 1 hour 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 1 hour 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 3 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 4 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

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