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

Find Hotels with a Pool in Sugarloaf Key, FL from CA $188

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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 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.
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.
CA $167
CA $188 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
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.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

2. 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.
CA $183
CA $252 total
includes taxes & fees
Nov 15 - Nov 16
Parmer's 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 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.

3. 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.
CA $166
CA $269 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Key West Resort & Marina
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.
A waterfront property with a two-story building, a covered outdoor area, and a dock.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
CA $209
CA $607 total
includes taxes & fees
Oct 28 - Oct 29
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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.
CA $197
CA $222 total
includes taxes & fees
Oct 26 - Oct 27
Looe Key Reef Resort
A large swimming pool with lounge chairs and palm trees.
Sports facility
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.'

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.
CA $148
CA $206 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A balcony with wicker furniture and a view of the ocean and palm trees.
A hotel room with a balcony, a bed, a desk, and two chairs.
Breakfast area

7. 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.
CA $237
CA $267 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.

8. 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.
CA $163
CA $223 total
includes taxes & fees
Oct 28 - Oct 29
Fairfield by Marriott Inn & Suites Key West at 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 room with a large bed, a desk, a chair, a small table, and a balcony with a view of palm trees.
A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

9. 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.
CA $151
CA $217 total
includes taxes & fees
Oct 29 - Oct 30
DoubleTree Resort by Hilton Grand Key - Key West
A marina with boats, a dock, and a white building with a balcony.
A waterfront property with a covered porch, a boat dock, and a clear sky.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
CA $266
CA $684 total
includes taxes & fees
Oct 31 - Nov 1
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 6 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 7 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 11 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 12 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 13 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 13 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 16 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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