Hotels with connecting rooms in Sugarloaf Key
Florida
United States of America
Hotels with connecting rooms
Expedia.com.sg

Sugarloaf Key Travel Guide Hotels in Sugarloaf Key Flights to Sugarloaf Key Things to do in Sugarloaf Key Car Hire in Sugarloaf Key Sugarloaf Key Holiday Packages Holiday Rentals in Sugarloaf Key

A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Hotels with connecting rooms in Sugarloaf Key

Where to?

Dates

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

November 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

December 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

Travellers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Sugarloaf Key hotels with connecting rooms

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

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 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 tropical resort with palm trees, a pool, and a wooden building.

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.

View all properties

Explore a world of travel with Expedia

Lodging
Flights
Packages
Cars
Holiday Rentals
Things to Do

Hotels with Swimming Pools in Big Pine Key
Standard Link for Hotels with Swimming Pools in Big Pine Key
Big Pine Key Hotels
Standard Link for Big Pine Key Hotels
Resorts in Big Pine Key
Standard Link for Resorts in Big Pine Key
Cow Key Hotels
Standard Link for Cow Key Hotels
Houseboats in Cow Key
Standard Link for Houseboats in Cow Key
Hotels with Bars / Lounges in Cudjoe Key
Standard Link for Hotels with Bars / Lounges in Cudjoe Key
Hotels with Swimming Pools in Key Colony Beach
Standard Link for Hotels with Swimming Pools in Key Colony Beach
All Inclusive Hotels and Resorts in Key West
Standard Link for All Inclusive Hotels and Resorts in Key West
Beach Resorts in Key West
Standard Link for Beach Resorts in Key West
Boutique Hotels in Key West
Standard Link for Boutique Hotels in Key West
Budget Hotels in Key West
Standard Link for Budget Hotels in Key West
Business Hotels in Key West
Standard Link for Business Hotels in Key West
Family friendly Hotels in Key West
Standard Link for Family friendly Hotels in Key West
Gay friendly Hotels in Key West
Standard Link for Gay friendly Hotels in Key West
Golf Hotels in Key West
Standard Link for Golf Hotels in Key West
Hotels with Airport Shuttle in Key West
Standard Link for Hotels with Airport Shuttle in Key West
Hotels with Bars / Lounges in Key West
Standard Link for Hotels with Bars / Lounges in Key West
Hotels with free wifi in Key West
Standard Link for Hotels with free wifi in Key West
Hotels with kitchenette in Key West
Standard Link for Hotels with kitchenette in Key West
Hotels with parking in Key West
Standard Link for Hotels with parking in Key West
Hotels with Swimming Pools in Key West
Standard Link for Hotels with Swimming Pools in Key West
Hotels with shuttle in Key West
Standard Link for Hotels with shuttle in Key West
Pet friendly Hotels in Key West
Standard Link for Pet friendly Hotels in Key West
Romantic Hotels in Key West
Standard Link for Romantic Hotels in Key West
Castles in Little Torch Key
Standard Link for Castles in Little Torch Key
Scuba Diving Hotels in Little Torch Key
Standard Link for Scuba Diving Hotels in Little Torch Key
Beach Resorts in Lower Keys
Standard Link for Beach Resorts in Lower Keys
Hotels with Childcare in Marathon
Standard Link for Hotels with Childcare in Marathon
Hotels with kitchenette in Marathon
Standard Link for Hotels with kitchenette in Marathon
Romantic Hotels in Marathon
Standard Link for Romantic Hotels in Marathon
Gay friendly Hotels in Marathon Shores
Standard Link for Gay friendly Hotels in Marathon Shores
Cottages in No Name Key
Standard Link for Cottages in No Name Key
Inns in Rockland Key
Standard Link for Inns in Rockland Key
Apartments in Stock Island
Standard Link for Apartments in Stock Island
Summerland Key Hotels
Standard Link for Summerland Key Hotels
Gay friendly Hotels in Sunset Key
Standard Link for Gay friendly Hotels in Sunset Key

Flights to Little Torch Key
Standard Link for Flights to Little Torch Key
Delta Philadelphia (PHL) to Key West (EYW) flights
Standard Link for Delta Philadelphia (PHL) to Key West (EYW) flights
Flights from Little Torch Key
Standard Link for Flights from Little Torch Key
Flights from Boca Chica Key
Standard Link for Flights from Boca Chica Key
Flights from Big Torch Key
Standard Link for Flights from Big Torch Key
Flights from Melody Key
Standard Link for Flights from Melody Key
Flights from Middle Torch Key
Standard Link for Flights from Middle Torch Key
Flights from Albany (ALB) to Key West (EYW)
Standard Link for Flights from Albany (ALB) to Key West (EYW)
Flights from Aur (AUL) to Key West (EYW)
Standard Link for Flights from Aur (AUL) to Key West (EYW)
Flights from Nashville (BNA) to Key West (EYW)
Standard Link for Flights from Nashville (BNA) to Key West (EYW)
Flights from Basel (BSL) to Key West (EYW)
Standard Link for Flights from Basel (BSL) to Key West (EYW)
Flights from Clemson (CEU) to Key West (EYW)
Standard Link for Flights from Clemson (CEU) to Key West (EYW)
Flights from Chattanooga (CHA) to Key West (EYW)
Standard Link for Flights from Chattanooga (CHA) to Key West (EYW)
Flights from Charlottesville (CHO) to Key West (EYW)
Standard Link for Flights from Charlottesville (CHO) to Key West (EYW)
Flights from Corpus Christi (CRP) to Key West (EYW)
Standard Link for Flights from Corpus Christi (CRP) to Key West (EYW)
Flights from Cincinnati (CVG) to Key West (EYW)
Standard Link for Flights from Cincinnati (CVG) to Key West (EYW)
Flights from Daytona Beach (DAB) to Key West (EYW)
Standard Link for Flights from Daytona Beach (DAB) to Key West (EYW)
Flights from Washington (DCA) to Key West (EYW)
Standard Link for Flights from Washington (DCA) to Key West (EYW)
Flights from Fort Lauderdale (FLL) to Key West (EYW)
Standard Link for Flights from Fort Lauderdale (FLL) to Key West (EYW)
Flights from Gainesville (GNV) to Key West (EYW)
Standard Link for Flights from Gainesville (GNV) to Key West (EYW)
Flights from Gavle (GVX) to Key West (EYW)
Standard Link for Flights from Gavle (GVX) to Key West (EYW)
Flights from Washington (IAD) to Key West (EYW)
Standard Link for Flights from Washington (IAD) to Key West (EYW)
Flights from Jonesboro (JBR) to Key West (EYW)
Standard Link for Flights from Jonesboro (JBR) to Key West (EYW)
Flights from Jamestown (JHW) to Key West (EYW)
Standard Link for Flights from Jamestown (JHW) to Key West (EYW)
Flights from Kitoi Bay (KKB) to Key West (EYW)
Standard Link for Flights from Kitoi Bay (KKB) to Key West (EYW)
Flights from Los Angeles (LAX) to Key West (EYW)
Standard Link for Flights from Los Angeles (LAX) to Key West (EYW)
Flights from London (LHR) to Key West (EYW)
Standard Link for Flights from London (LHR) to Key West (EYW)
Flights from West Palm Beach (LNA) to Key West (EYW)
Standard Link for Flights from West Palm Beach (LNA) to Key West (EYW)
Flights from Merida (MID) to Key West (EYW)
Standard Link for Flights from Merida (MID) to Key West (EYW)
Flights from Moscow (MOW) to Key West (EYW)
Standard Link for Flights from Moscow (MOW) to Key West (EYW)
Flights from Metlakatla (MTM) to Key West (EYW)
Standard Link for Flights from Metlakatla (MTM) to Key West (EYW)
Flights from New York (NYC) to Key West (EYW)
Standard Link for Flights from New York (NYC) to Key West (EYW)
Flights from Jacksonville (OAJ) to Key West (EYW)
Standard Link for Flights from Jacksonville (OAJ) to Key West (EYW)
Flights from Chicago (ORD) to Key West (EYW)
Standard Link for Flights from Chicago (ORD) to Key West (EYW)
Flights from Oviedo (OVD) to Key West (EYW)
Standard Link for Flights from Oviedo (OVD) to Key West (EYW)
Flights from Owensboro (OWB) to Key West (EYW)
Standard Link for Flights from Owensboro (OWB) to Key West (EYW)
Flights from West Palm Beach (PBI) to Key West (EYW)
Standard Link for Flights from West Palm Beach (PBI) to Key West (EYW)
Flights from Peppimenarti (PEP) to Key West (EYW)
Standard Link for Flights from Peppimenarti (PEP) to Key West (EYW)
Flights from Phoenix (PHX) to Key West (EYW)
Standard Link for Flights from Phoenix (PHX) to Key West (EYW)
Flights from Providence (PVD) to Key West (EYW)
Standard Link for Flights from Providence (PVD) to Key West (EYW)
Flights from St. Louis (STL) to Key West (EYW)
Standard Link for Flights from St. Louis (STL) to Key West (EYW)
Flights from St. Louis (SUS) to Key West (EYW)
Standard Link for Flights from St. Louis (SUS) to Key West (EYW)
Flights from Newburgh (SWF) to Key West (EYW)
Standard Link for Flights from Newburgh (SWF) to Key West (EYW)
Flights from Thomasville (TVI) to Key West (EYW)
Standard Link for Flights from Thomasville (TVI) to Key West (EYW)
Flights from St. Augustine (UST) to Key West (EYW)
Standard Link for Flights from St. Augustine (UST) to Key West (EYW)
Flights from St. John's (YYT) to Key West (EYW)
Standard Link for Flights from St. John's (YYT) to Key West (EYW)

Visit Eden Pines
Standard Link for Visit Eden Pines
Boca Chica Nude Beach
Standard Link for Boca Chica Nude Beach
Visit Lower Florida Keys
Standard Link for Visit Lower Florida Keys
Visit Rockland Key
Standard Link for Visit Rockland Key
Visit Stock Island
Standard Link for Visit Stock Island
Visit Sugarloaf Key
Standard Link for Visit Sugarloaf Key

Economy Rent a Car Rental Cars in Little Torch Key
Standard Link for Economy Rent a Car Rental Cars in Little Torch Key
Goldcar Key’n Go Rental Cars in Lower Florida Keys
Standard Link for Goldcar Key’n Go Rental Cars in Lower Florida Keys
Localiza Rental Cars in Middle Torch Key
Standard Link for Localiza Rental Cars in Middle Torch Key
Mex Rent A Car Rental Cars in Cudjoe Key
Standard Link for Mex Rent A Car Rental Cars in Cudjoe Key
Midway Car Rental Rental Cars in Sugarloaf Key
Standard Link for Midway Car Rental Rental Cars in Sugarloaf Key
Rent A Wreck Rental Cars in Sugarloaf Key
Standard Link for Rent A Wreck Rental Cars in Sugarloaf Key

Lower Keys Holiday Rentals
Standard Link for Lower Keys Holiday Rentals

Things to do in Big Pine Key
Standard Link for Things to do in Big Pine Key

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

Explore a world of travel with Expedia