Sugarloaf Key Cottages

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 prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Sugarloaf Key cottages

1. Old Wooden Bridge Resort and Marina

Punta Brisa

Kathy

includes taxes & fees

1 Sept - 2 Sept

2. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

BRIAN S.

includes taxes & fees

11 Sept - 12 Sept

3. The Dancing Rooster: 2 Blocks from Duval in Old Town.

Old Town Key West

Mercedes A.

includes taxes & fees

19 Aug - 20 Aug

View all properties

Find holiday rentals that suit your style

Houseboats

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"This is our second trip to the Keys this year, and first time at this property. We found our home away from home and will stay here again next time! Everything is quality!"

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"We looked at a lot of the local hotels before choosing to go with one of the big chains. The things we saw in the reviews of the local places...street noise, no air conditioning or air that didn't work well, small rooms, places in need of renovation, etc, etc. So the chain was the "safe" choice and honestly it didn't disappoint. It was clean, the air worked, it was a good location, the beds were comfortable, they have a really neat sparkling water machine in the lobby, they have free pina coladas or margaritas, the staff was friendly. The room was quiet. I don't know what else we could have asked for."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"5 star resort. Well maintained property. Housekeeping was incredible. The ladies doing the daily drink making classes and activities poolside were hysterical and made for a good time! Duval street right outside property made for easy shopping excursions. The property coffee shop and breakfast bar offered great choices. Will definitely be back!"

Find out more about Sugarloaf Key