Top Hotels with connecting rooms in Sugarloaf Key

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

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 availability on Sugarloaf Key Hotels with connecting rooms

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Sugarloaf Key hotels with connecting rooms

Sugar Loaf Lodge

Summerland Key

Oyuntseren

includes taxes & fees

26 Jul - 27 Jul

Duval House

Old Town Key West

Wendy S

includes taxes & fees

7 Jul - 8 Jul

Looe Key Reef Resort

Summerland Key

includes taxes & fees

16 Jul - 17 Jul

Hyatt Centric Key West Resort and Spa

Key West Historic District

JASON

includes taxes & fees

29 Jun - 30 Jun

Beachside Resort & Residences

Key West

Molly

includes taxes & fees

1 Jul - 2 Jul

The Reach Key West, Curio Collection by Hilton

Old Town Key West

includes taxes & fees

14 Jul - 15 Jul

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Brendan

includes taxes & fees

8 Jul - 9 Jul

Ibis Bay Beach Resort

Northside Resort

megan Renae

includes taxes & fees

7 Jul - 8 Jul

View all properties

Top Sugarloaf Key Hotel Reviews

Pier House Resort & Spa

10/10 Excellent

"Our stay was amazing. I’ve wanted to stay at the Pier House for a long time for a few reasons. The location on the water and the history the property has with the late Jimmy Buffett. The Chart Room bar is a must visit for all who like old fashioned bars that haven’t changed in 55 years. The beach area and bar was wonderful as was the rest of the lush jungle like property. We will be back! The staff was attentive and professional!"

The Perry Hotel & Marina Key West

10/10 Excellent

"Absolutely loved this property. Perfect location, off to the side so not directly in loud and busy Key West but close enough to run and grab a key lime slice after dinner! Property is beautiful, hotel smells so nice. The absolute only thing and perhaps it’s not even the hotels fault, the marina has so much trash floating in the water. We loved watching all the jellyfish, nurse sharks and tarpon swimming around but hated that they were dodging trash. Will stay again for sure!"

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"The resort itself was beautiful, and our room was spacious and comfortable. The property has a lot to offer, and we were looking forward to a relaxing vacation. Unfortunately, the first three nights of our stay were anything but relaxing due to a business event being held at the resort. Our room was located above or near the ballroom, and we could hear the loud bass from the music being played during the events. The noise carried into our room late into the night and made it difficult to relax. We complained to the front desk and the first response was that they would ask the event to turn down the music. The second response was this happens a lot when events are held here. The third response was from the security staff who got us a room credit which we appreciated but it was not his job to do what management should have done. To make matters worse, on our very first morning we were awakened at 6:30 a.m. by the same music. Throughout our stay, various event-related activities around the resort created additional disruptions that took away from the peaceful atmosphere we had expected. While the resort and our accommodations were excellent, the noise and disturbances associated with the business event significantly impacted our experience. Guests seeking a quiet, relaxing vacation may want to inquire about scheduled conferences or large events before booking."

Frequently asked questions

Why book your hotel with connecting rooms in Sugarloaf Key with Expedia?

Expedia makes it easy to find your dream hotel with connecting rooms in Sugarloaf Key. Getting away with the family? Find your way to the filters to search for stays with perks like a water park. If you have a budget, choose how much you're willing to spend and your preferred hotel star rating. We'll help you find the perfect stay whatever your plans or bank balance.

How can I find cheap hotels with connecting rooms in Sugarloaf Key?

The best way to find cheap hotels with connecting rooms in Sugarloaf Key is with Expedia's easy-to-use filter tool. Refine your search results by budget, star rating and amenities to snag awesome bargains in just a few clicks.

What is there to do in Sugarloaf Key near my hotel with connecting rooms?

If you want to explore the best of Sugarloaf Key, don't miss Florida Keys Beaches. It's a winner with tourists and locals alike.

Explore a world of travel with Expedia

Lower Keys Holiday Rentals

Things to do in Big Pine Key

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Sugarloaf Key Hotels with connecting rooms

Our top choices for Sugarloaf Key hotels with connecting rooms

Sugar Loaf Lodge

Duval House