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

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Our top choices for Sugarloaf Key hotels with shopping nearby

Terrace/patio

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is AED 1,069
AED 2,570 total
includes taxes & fees
11 Aug - 12 Aug
Starlight Serenity - Hideaway with Stunning Views
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (351 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is AED 379
AED 943 total
includes taxes & fees
12 Jul - 13 Jul
Old Wooden Bridge Resort and Marina
Exterior

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,009 reviews)
"Awesome place!"
United States
Meredith
The price is AED 460
AED 637 total
includes taxes & fees
12 Jul - 13 Jul
Parmer's Resort
Outdoor pool, a heated pool

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (72 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is AED 1,833
AED 4,763 total
includes taxes & fees
3 Aug - 4 Aug
One of the very few beach houses with a daily, rental license in the Keys.
Marina

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Had a great time. Clean and comfortable home. "
United States
Chris H.
The price is AED 868
AED 2,405 total
includes taxes & fees
19 Jul - 20 Jul
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Outdoor dining

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

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (31 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is AED 1,650
AED 2,990 total
includes taxes & fees
4 Aug - 5 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Outdoor dining

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (21 reviews)
"Great location, beautiful rental very clean with access to the complex pool and also has a golf cart!"
United States
Michael C.
The price is AED 1,639
AED 3,593 total
includes taxes & fees
12 Jul - 13 Jul
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
A heated pool

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is AED 868
AED 2,405 total
includes taxes & fees
15 Jul - 16 Jul
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Terrace/patio

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is AED 1,735
AED 3,462 total
includes taxes & fees
16 Jul - 17 Jul
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Terrace/patio

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
Cudjoe Key
8.0 out of 10, Very Good, (3 reviews)
"We had a great stay enjoyed the short stay we had "
United States
Jeremy B.
The price is AED 1,504
AED 3,180 total
includes taxes & fees
23 Jul - 24 Jul
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
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.
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Top Sugarloaf Key Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Our first trip to Key West and Pier House did not disappoint! Aside from the best location, this hotel was like an oasis when you wanted to get away from the We would never stay anywhere else, this hotel is"
Julie 6-night trip
Posted less than an hour ago
Pier House Resort & Spa

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