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

Sugarloaf Key Hotels with Swimming Pool

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Check availability on Sugarloaf Key Hotels with Swimming Pools

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 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 reception area with a wooden sculpture, a reception desk, a computer, and a television.
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.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
RM486
RM546 total
includes taxes & fees
27 Oct - 28 Oct
Sugar Loaf Lodge
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.
View from room
Breakfast area

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.
RM690
RM776 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key West FL
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 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.

3. 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.
RM533
RM733 total
includes taxes & fees
15 Nov - 16 Nov
Parmer's Resort
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.

4. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
RM573
RM644 total
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.
A modern office space with a reception desk, computer, and seating area.
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.

5. 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.
RM474
RM648 total
includes taxes & fees
28 Oct - 29 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A large swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
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.
RM432
RM601 total
includes taxes & fees
29 Oct - 30 Oct
Hilton Garden Inn Key West / The Keys Collection
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 clear view of turquoise ocean water and a blue sky with clouds.
A marina with numerous boats docked, a swimming pool, and palm trees.

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.
RM482
RM781 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 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.

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.
RM437
RM630 total
includes taxes & fees
29 Oct - 30 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.
A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

9. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
  • Savour the sun in this poolside paradise with tropical gardens and a relaxing hot tub.
RM649
RM730 total
includes taxes & fees
27 Oct - 28 Oct
Courtyard by Marriott Key West Waterfront
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A two-story building with a balcony, surrounded by tropical vegetation.
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.

10. 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.
RM2,113
RM3,984 total
includes taxes & fees
26 Oct - 27 Oct
Atlantic View Luxury Villa with Pool
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

8/10 Good
"Loved the wristband key to the room. The room was clean, the bed was comfortable. The noise from the A/C was annoying…off and on all night long. The water/ice machine outside our room did not work, however, we loved the fruit flavored water in the lobby. Coffee machine in room was nice feature. We visited all 3 pools. They were nice but not cleaned as should be. One was pretty cloudy so we didn’t go back to that one. Seems like the drinkers didn’t take time out to use restrooms. All in all, it was a nice place at the southern end of Duval St."
Gina M 4-night trip
Posted 5 hours ago
Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"This is the third time that I have stayed there It's very unique They've got a nice restaurant a pool sits right on the Bay and they have their own wildlife They have Galapagos turtles They have lots of ibises running around plenty of iguanas One of those talking birds I forget what type it was greets you as you go in through the front door It appears to me that it's been remodeled in the past 5 to 10 years so it's clean and bright with great views this past week when I was there I had the entire beach area to myself and you get your own little patio to hang out I recommend it Everyone that I know that's going there"
Eric 3-night trip
Posted 6 hours ago
Ibis Bay Beach Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"N/A"
Richard 3-night trip
Posted 10 hours ago
Opal Key Resort & Marina, Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Estephany at the front desk is wonderful! The food is delicious! One of the best breakfast omelets. I enjoyed the burger and the Mahi Mahi. Very tidy room!"
Aldo 3-night trip
Posted 11 hours ago
Winslow's Bungalows - Key West Historic Inns
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 12 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 12 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"great room, pool, laundry, tiki bar, staff"
Pamela 5-night trip
Posted 15 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 3 days ago
Hilton Garden Inn Key West / The Keys Collection

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