Our top choices for Sugarloaf Key hotels

Sugar Loaf Lodge

Summerland Key

Oyuntseren

₩222,326 total

includes taxes & fees

Jun 18 - Jun 19

Starlight Serenity - Hideaway w Stunning Views

Summerland Key

₩1,223,922 total

includes taxes & fees

Jun 15 - Jun 16

Outdoor pool, open 7:00 AM to 10:00 PM, free cabanas, sun loungers

Fairfield Inn and Suites by Marriott Key West

New Town

Valentina

₩268,672 total

includes taxes & fees

Jun 24 - Jun 25

The Southernmost Inn - Adults Only

Old Town Key West

Sharon

₩272,071 total

includes taxes & fees

Jun 16 - Jun 17

Ibis Bay Beach Resort

Northside Resort

megan Renae

₩270,014 total

includes taxes & fees

Jun 14 - Jun 15

Parmer's Resort

Summerland Key

Emmanuel

₩358,647 total

includes taxes & fees

Jun 23 - Jun 24

Looe Key Reef Resort

Summerland Key

Dwain

₩268,540 total

includes taxes & fees

Jul 8 - Jul 9

1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Punta Brisa

Sofia

₩420,854 total

includes taxes & fees

Jun 24 - Jun 25

Outdoor pool, open 7:00 AM to 9:00 PM, cabanas (surcharge), sun loungers

DoubleTree Resort by Hilton Grand Key - Key West

Key West

Clara

₩311,918 total

includes taxes & fees

Jun 21 - Jun 22

Hyatt Vacation Club at Windward Pointe, Key West

Key West

Jennifer

₩625,766 total

includes taxes & fees

Jun 14 - Jun 15

Duval Inn

Old Town Key West

Daniel

₩310,949 total

includes taxes & fees

Jun 15 - Jun 16

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Key West Historic District

Troy

₩295,356 total

includes taxes & fees

Jun 15 - Jun 16

Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Key West FL

Key West

Michael

₩394,658 total

includes taxes & fees

Jun 14 - Jun 15

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

Omar

₩289,524 total

includes taxes & fees

Jul 1 - Jul 2

Ocean View 3BR Condo with Rooftop Balcony | Balcony

Beachside Resort & Residences

Key West

Molly

₩365,736 total

includes taxes & fees

Jun 17 - Jun 18

Courtyard by Marriott Key West Waterfront

Northside Resort

Kalena

₩308,488 total

includes taxes & fees

Jun 16 - Jun 17

Paradise Inn Key West - Adults Only

Old Town Key West

Nicholas

₩263,029 total

includes taxes & fees

Jun 15 - Jun 16

Beach nearby, white sand, beach cabanas, sun loungers

Amsterdam's Curry Mansion Inn

Key West Historic District

Curtis

₩506,526 total

includes taxes & fees

Jun 14 - Jun 15

The Cabana Inn Key West - Adults Only

Old Town Key West

Nickolas

₩300,030 total

includes taxes & fees

Jun 14 - Jun 15

The Palms Hotel

Old Town Key West

Victoria

₩283,119 total

includes taxes & fees

Jun 30 - Jul 1

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Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colorful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkeling spots.

See all hotels in Sugarloaf Key

Top Sugarloaf Key Hotel Reviews

Blue Flamingo Resort Key West

10/10 Excellent

"We loved the late 70's - 80's music with a few newer songs thrown in there!! The Blue Flamingo could be whatever you wanted it to be! Pools, any game you could think of, inside and out! Easy to travel around by bus, trolly, Uber. Made a point to hit Hermits Key Lime Pie, The Butterfly house, Sloppy Joes of course, and Hemingway's! Just a wonderful place to experience and have plans to go back! Minutes from the airport! Lovely over all! June 7- 11, 2026"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"We had a wonderful 4-night stay. Location was excellent for us, as we did not want to be in the hustle of Duval at night. It was so quiet and airplanes didn’t bother or wake us. Condo had everything we needed, was spacious, and well-maintained. We never had trouble finding chairs at the pool. 15-20 min Uber ride if we didn’t feel like driving to Old Town. The Trolley Tour also has a stop at the hotel next door. If we ever return, this is where we would stay."

Margaritaville Beach House Key West

8/10 Good

"I have no complaints about the room and or housekeeping. The only thing I can say that needs improvement is some of the upkeep on the exterior of the buildings and the elevator was extremely hot inside. It was like riding in a sauna every time. Otherwise, the stay was very nice."

The Reach Key West, Curio Collection by Hilton

6/10 Okay

"Stayed the first week of June. Rooms were nice but property felt very dated. Not a lot of beaches in Key West so was excited to find a property with a man made one. Unfortunately there was a ton of seaweed and it was essentially not usable. The pool was small and underwhelming. Food and drink on the property was outrageously expensive. $28 for a GLASS of mediocre white win. Nuts. The concierge was basically unwilling or unable to give us basic suggestions for local restaurants. The valets were great as was front desk staff. Overall a good property and good location, the place just really needs a facelift and more reasonable prices in the restaurant."