Hotels with connecting rooms in Sugarloaf Key
Florida
United States of America
Hotels with connecting rooms
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A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Hotels with connecting rooms in Sugarloaf Key

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your current months are November, 2026 and December, 2026.

November 2026

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Our top choices for Sugarloaf Key hotels with connecting rooms

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

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

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

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

1. Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property

Summerland Key

8.2 out of 10, Very good, (1,000 reviews)

8.2/10

Very good

(1,000 reviews)

"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."

Mariia

The price is S$143

S$143

includes taxes & fees

30 Nov - 1 Dec

Sugar Loaf Lodge

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A marina with boats docked, a swimming pool, and palm trees.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

2. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4.0 star property

Stock Island

9.4 out of 10, Exceptional, (1,315 reviews)

9.4/10

Exceptional

(1,315 reviews)

"Good place to stay."

Dharmesh Raju

The price is S$238

S$238

includes taxes & fees

30 Nov - 1 Dec

The Perry Hotel & Marina Key West

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

3. Looe Key Reef Resort

Looe Key Reef Resort

2.5 star property

Summerland Key

7.8 out of 10, Good, (1,000 reviews)

7.8/10

Good

(1,000 reviews)

"Everything was amazing staff was very accommodating would definitely recommend"

Stephen

The price is S$232

S$232

includes taxes & fees

10 Nov - 11 Nov

Looe Key Reef Resort

A marina with boats docked, a pool area, and a building with a white facade.

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.

4. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4.0 star property

Stock Island

9.0 out of 10, Wonderful, (1,795 reviews)

9.0/10

Wonderful

(1,795 reviews)

"Great location and great staff!!"

Kevin

The price is S$245

S$245

includes taxes & fees

15 Nov - 16 Nov

Hilton Key West Resort & Marina

A 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.'

A modern living room with a sectional sofa, a small round table, and a potted plant.

5. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 star property

New Town

8.2 out of 10, Very good, (1,356 reviews)

8.2/10

Very good

(1,356 reviews)

"Room was very comfortable, staff was very helpful and breakfast was good"

Darlene

The price is S$202

S$202

includes taxes & fees

15 Nov - 16 Nov

Hilton Garden Inn Key West / The Keys Collection

A pool area with lounge chairs and gazebos, surrounded by palm trees.

A spacious room with a high ceiling, large windows, and a view of palm trees.

A modern dining area with multiple tables and chairs, large windows, and ceiling fans.

An outdoor patio area with tables and chairs, umbrellas, and palm trees.

6. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property

Key West

8.4 out of 10, Very good, (1,133 reviews)

8.4/10

Very good

(1,133 reviews)

"The hotel was a spectacular place near the airport."

Suset

The price is S$221

S$221

includes taxes & fees

15 Nov - 16 Nov

DoubleTree Resort by Hilton Grand Key - Key West

A hotel with a swimming pool, sun loungers, and palm trees.

A spacious living area with a sofa, chairs, a coffee table, and a swing chair.

A beachside resort with palm trees, outdoor seating, and a food truck.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

7. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property

New Town

8.6 out of 10, Excellent, (2,778 reviews)

8.6/10

Excellent

(2,778 reviews)

"Nice resort very family friendly"

Sigrid A

The price is S$253

S$253

includes taxes & fees

15 Nov - 16 Nov

Blue Flamingo Resort Key West

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

8. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4.0 star property

Old Town Key West

8.4 out of 10, Very good, (1,010 reviews)

8.4/10

Very good

(1,010 reviews)

"Great place"

Nguyen

The price is S$430

S$430

includes taxes & fees

23 Nov - 24 Nov

Casa Marina Key West, Curio Collection by Hilton

A hotel with a swimming pool, balconies, and a view of the sea.

A balcony with a view of the ocean, a table, chairs, and a railing.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

9. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4.0 star property

Key West Historic District

9.2 out of 10, Wonderful, (1,003 reviews)

9.2/10

Wonderful

(1,003 reviews)

"Wonderful property with wonderful staff"

Michael Joseph

The price is S$458

S$458

includes taxes & fees

1 Dec - 2 Dec

Hyatt Centric Key West Resort and Spa

A beach with a wooden pier, palm trees, and beach umbrellas.

A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

An outdoor dining area with tables and chairs, overlooking the ocean.

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

10. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4.0 star property

Old Town Key West

8.6 out of 10, Excellent, (1,066 reviews)

8.6/10

Excellent

(1,066 reviews)

"Had a great experience to celebrate my birthday here."

Rowena

The price is S$380

S$380

includes taxes & fees

30 Nov - 1 Dec

The Reach Key West, Curio Collection by Hilton

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Hotels with connecting rooms in Sugarloaf Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sugarloaf Key hotels with connecting rooms

1. Sugar Loaf Lodge

2. The Perry Hotel & Marina Key West

3. Looe Key Reef Resort

4. Hilton Key West Resort & Marina

5. Hilton Garden Inn Key West / The Keys Collection

6. DoubleTree Resort by Hilton Grand Key - Key West

7. Blue Flamingo Resort Key West

8. Casa Marina Key West, Curio Collection by Hilton

9. Hyatt Centric Key West Resort and Spa

10. The Reach Key West, Curio Collection by Hilton

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