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

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Sugarloaf Key cottages

Exterior

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (352 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is SAR 387
SAR 964 total
includes taxes & fees
13 Jul - 14 Jul
Old Wooden Bridge Resort and Marina
Property grounds

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 SAR 1,686
SAR 3,057 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

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is SAR 1,314
SAR 2,308 total
includes taxes & fees
2 Aug - 3 Aug
Canal front, dockage, 2 bedroom, 2 bath
Property grounds

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"All was excellent "
United States
Bryan M.
The price is SAR 1,201
SAR 2,196 total
includes taxes & fees
24 Jul - 25 Jul
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Exterior

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (173 reviews)
"Great place "
United States
David
The price is SAR 760
SAR 1,439 total
includes taxes & fees
15 Jul - 16 Jul
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
The price is SAR 760
SAR 1,514 total
includes taxes & fees
1 Aug - 2 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
Get your ISLAND STLYE on!
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (31 reviews)
"Great location, super clean. Great host communication. Thanks for a terrific stay!"
United States
Juleigh N.
The price is SAR 1,201
SAR 2,226 total
includes taxes & fees
5 Aug - 6 Aug
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

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

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (148 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The price is SAR 1,378
SAR 2,447 total
includes taxes & fees
1 Aug - 2 Aug
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"This was a wonderful property! The rooms were clean and spacious, parking was ample, the pool and surrounding enjoyment area was wonderful and fun, the food and drinks were good, the lobby was inviting and had enough lounging and check-in space, they offered free treats for furry friends, the shuttle was comfortable and consistently on-time, and they have lots of nice swag for purchase. My only issue was, since we booked on Expedia/hotels.com, and paid for three people, we ONLY were given two breakfast vouchers. We questioned this, and they said it's just how their listing on Expedia is - no real explanation or correction of the error. BTW, although the listing states this is a 21+ hotel, kids are definitely welcome."
Shari 2-night trip
Posted less than an hour ago
Havana Cabana at Key West

Frequently asked questions

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