Search Cottages in Lower Sugarloaf Key

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Lower Sugarloaf Key cottages

Exterior
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (278)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina
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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (49)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is €277
includes taxes & fees
14 Dec - 15 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is €287
includes taxes & fees
15 Dec - 16 Dec
Charming cottages, dockage, pool, just minutes to Key West
Terrace/patio
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (25)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
The price is €349
includes taxes & fees
14 Dec - 15 Dec
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (90)
"Nice place to vacation "
United States
Kevin D.
The price is €302
includes taxes & fees
13 Dec - 14 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Marina
Living Life Dockside

Living Life Dockside

Living Life Dockside
Stock Island
The price is €542
includes taxes & fees
4 Jan - 5 Jan 2026
Living Life Dockside
Exterior
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
10.0 out of 10, Exceptional, (131)
"Great place to stay"
United States
JEFFREY Z.
The price is €628
includes taxes & fees
19 Dec - 20 Dec
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Exterior
Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community
Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
Beautiful Cottage & Amenities in Gated Community
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

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
9.6 out of 10, Exceptional, (10)
"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."
United States
Michael M.
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
The price is €354
includes taxes & fees
17 Dec - 18 Dec
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (27)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is €354
includes taxes & fees
15 Dec - 16 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Exterior
Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (10)
"Great place to stay! "
United States
sarah R.
Find your zen at HIDDEN TREASURE
Terrace/patio
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is €352
includes taxes & fees
18 Dec - 19 Dec
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Terrace/patio
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is €366
includes taxes & fees
20 Dec - 21 Dec
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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 Lower Sugarloaf Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Great room, good location to Duval Street. Nice and quiet for good sleep. "
Tracy D 3-night trip
Posted 1 day ago
Winslow's Bungalows - Key West Historic Inns

Find out more about Lower Sugarloaf Key

Lower Sugarloaf Key Cottages information

Number of reviews
808
Accommodation
114 Cottages
Lowest Price
€277
Highest Price
€628

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