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

Find Historic Hotels in Sugarloaf Key, FL

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Check availability on Sugarloaf Key Historic Hotels

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Sugarloaf Key historic hotels

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
NT$2,859
NT$4,838 total
includes taxes & fees
Aug 16 - Aug 17
Pegasus International Hotel

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
NT$6,375
NT$7,172 total
includes taxes & fees
Aug 25 - Aug 26
Amsterdam's Curry Mansion Inn
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Top Sugarloaf Key Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"Next to the airport and away from the center of town"
Amelia 4-night trip
Posted less than an hour ago
Hyatt Vacation Club at Windward Pointe, Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Love it there. Thor was our third year. And we brought fiends this time. They also loved it."
David 5-night trip
Posted 2 hours ago
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"This was a great experience. The staff was helpful. The cleaning service was nice and I was able to get what I needed for my room quickly. The amenities covered everything we needed to use the dishwasher and laundry machine in our unit. The dishes and utensils were not cheap looking which was nice. The only draw back we felt was the water at the beach area could have been cleaner. We had to travel to another area to go in the water. Other than that I would recommend this place to anyone and I will come back again soon."
Renee 5-night trip
Posted 6 hours ago
Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"The staff was very nice and helpful"
Christopher 4-night trip
Posted 8 hours ago
Blue Flamingo Resort Key West
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"Nice"
Steve 3-night trip
Posted 9 hours ago
The Reach 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
"Pool area was great along with the bar. Free shuttle to Duval St was very handy"
Stephen 4-night trip
Posted 18 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Beautiful beach, helpful staff"
Cynthia 2-night trip
Posted 21 hours ago
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Love the Music at the adult pool, it didn't stink that much from the seaweed. No smell by the pool. Love the firepits by the beach and food"
maria 1-night trip
Posted 1 day ago
Casa Marina Key West, Curio Collection by Hilton
Southwinds Motel

Southwinds Motel

8/10 Good
"Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location."
Tracy 4-night trip
Posted 1 day ago
Southwinds Motel

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