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 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
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 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.
NT$3,859
NT$4,341 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
Breakfast area
A balcony with wicker furniture and a view of the ocean and palm trees.
View from room

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.
NT$5,516
NT$6,205 total
includes taxes & fees
Oct 25 - Oct 26
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.
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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

3. 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.
NT$3,765
NT$5,147 total
includes taxes & fees
Oct 29 - Oct 30
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
A bedroom with a bed, a ceiling fan, a balcony with a view, and a nightstand with a lamp.
A two-story building with a balcony, surrounded by tropical vegetation.

4. 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.
NT$16,781
NT$31,647 total
includes taxes & fees
Oct 26 - Oct 27
Atlantic View Luxury Villa with Pool
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 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.

5. 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.
NT$3,963
NT$5,517 total
includes taxes & fees
Nov 9 - Nov 10
Parmer's Resort
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

6. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
NT$4,548
NT$5,116 total
includes taxes & fees
Oct 26 - Oct 27
Looe Key Reef Resort
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 marina with numerous boats docked, a swimming pool, and palm trees.
A clear view of turquoise ocean water and a blue sky with clouds.

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.
NT$3,854
NT$6,245 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Key West Resort & Marina
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 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.

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.
NT$3,476
NT$5,005 total
includes taxes & fees
Oct 29 - Oct 30
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 multi-story hotel with balconies, palm trees, and a pool area.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A marina with boats docked, 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.
NT$3,052
NT$5,331 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina Key West
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 modern living room with a sectional sofa, a small round table, and a potted plant.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

10. 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.
NT$3,433
NT$4,774 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Garden Inn Key West / 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

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Pool was nice and clean place was very quiet nice."
mary-lou 7-night trip
Posted less than an hour ago
Beachside Resort & Residences
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 10 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 11 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 15 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 15 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 17 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 17 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
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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