Hotel with Pool in Sugarloaf Key: Find Hotel with Pool in Sugarloaf Key

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

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Our top choices for Sugarloaf Key hotels with a pool

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

A waterfront building with a flat roof, large windows, and a balcony.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

1. Sugar Loaf Lodge

Summerland Key

Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.

HK$934

HK$1,051 total

includes taxes & fees

29 Oct - 30 Oct

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.

A balcony with wicker furniture and a view of the ocean and palm trees.

2. Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

HK$1,326

HK$1,492 total

includes taxes & fees

25 Oct - 26 Oct

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

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 modern office space with a reception desk, computer, and seating area.

3. 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.

HK$911

HK$1,246 total

includes taxes & fees

28 Oct - 29 Oct

A balcony with a view of a pool area, palm trees, and outdoor seating.

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.

A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

4. 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.

HK$841

HK$1,211 total

includes taxes & fees

29 Oct - 30 Oct

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 modern restaurant with a wooden counter, seating area, and large windows.

A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

5. Courtyard by Marriott Key West Waterfront

Northside Resort

Savour the sun in this poolside paradise with tropical gardens and a relaxing hot tub.

HK$1,248

HK$1,404 total

includes taxes & fees

28 Oct - 29 Oct

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.

Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

6. Parmer's Resort

Summerland Key

Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.

HK$959

HK$1,335 total

includes taxes & fees

9 Nov - 10 Nov

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.'

7. Hilton Garden Inn Key West / The Keys Collection

New Town

Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.

HK$827

HK$1,151 total

includes taxes & fees

28 Oct - 29 Oct

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.

8. 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.

HK$927

HK$1,501 total

includes taxes & fees

28 Oct - 29 Oct

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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

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."

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"

Opal Key Resort & Marina, Key West

10/10 Excellent

"N/A"

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!"

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"All I can say is all aspects were fantastic"

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"

Beachside Resort & Residences

10/10 Excellent

"great room, pool, laundry, tiki bar, staff"

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”."

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Check availability on Sugarloaf Key Hotel with Pool

Our top choices for Sugarloaf Key hotels with a pool

1. Sugar Loaf Lodge

2. Hampton Inn Key West FL

3. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

4. DoubleTree Resort by Hilton Grand Key - Key West

5. Courtyard by Marriott Key West Waterfront

6. Parmer's Resort

7. Hilton Garden Inn Key West / The Keys Collection

8. Hilton Key West Resort & Marina

9. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

10. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Choose what matters most at hotels with a pool in Sugarloaf Key

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Ibis Bay Beach Resort

Opal Key Resort & Marina, Key West

Winslow's Bungalows - Key West Historic Inns

Casa Marina Key West, Curio Collection by Hilton

DoubleTree Resort by Hilton Grand Key - Key West

Beachside Resort & Residences

Hilton Garden Inn Key West / The Keys Collection

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