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

Sugarloaf Key Hotel Guide - Hotels with Pool in Sugarloaf Key, Summerland Key

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Check availability on Sugarloaf Key Hotels with 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.
€119
includes taxes & fees
26 Oct - 27 Oct
Sugar Loaf Lodge
A waterfront hotel with a pool, palm trees, and a wooden dock.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.
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.

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
includes taxes & fees
28 Oct - 29 Oct
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 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.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
€390
includes taxes & fees
22 Oct - 23 Oct
SAVE BIG $$$ 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.
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.

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.
€160
includes taxes & fees
15 Nov - 16 Nov
Parmer's Resort
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 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.

5. 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.
€148
includes taxes & fees
16 Nov - 17 Nov
The Perry Hotel & Marina Key West
A large swimming pool with lounge chairs and palm trees.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
Sports facility

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.
€131
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Key West / The Keys Collection
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 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.
€138
includes taxes & fees
29 Oct - 30 Oct
DoubleTree Resort by Hilton Grand Key - Key West
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 spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

8. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
€141
includes taxes & fees
26 Oct - 27 Oct
Looe Key Reef Resort
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.

9. 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
includes taxes & fees
28 Oct - 29 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

10. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
  • Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.
€166
includes taxes & fees
26 Oct - 27 Oct
Blue Flamingo Resort 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

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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