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Our top choices for Lower Florida Keys cottages

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
$241 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
Old Wooden Bridge Resort and Marina

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, (28)
"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.
$341 nightly
The price is $375
Dec 21 - Dec 22
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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.
$297 nightly
The price is $330
Dec 20 - Dec 21
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Bad need of repair....rust....no boat ramp......shallow water....screened in porch was aweful with holes in the screens and lots of mosquitos and rusted grill."
United States
Debra M.
$257 nightly
The price is $285
Dec 20 - Dec 21
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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, (12)
"The owners were fantastic to deal with and the house was great. "
United States
Anonymous traveler
$348 nightly
The price is $387
Dec 23 - Dec 24
Total with taxes and fees
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (89)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
$334 nightly
The price is $370
Dec 21 - Dec 22
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (54)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
$648 nightly
The price is $710
Dec 24 - Dec 25
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4

Living Life Dockside

Living Life Dockside
Stock Island
$560 nightly
The price is $622
Jan 4 - Jan 5, 2026
Total with taxes and fees
Living Life Dockside

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
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

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, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
$684 nightly
The price is $759
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

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, (75)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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.
$351 nightly
The price is $387
Dec 20 - Dec 21
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

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, (52)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$286 nightly
The price is $317
Dec 20 - Dec 21
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$315 nightly
The price is $349
Dec 27 - Dec 28
Total with taxes and fees
Cottage with swimming pool and dockage, just minutes to Key West!

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)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
$540 nightly
The price is $594
Jan 7 - Jan 8, 2026
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$429 nightly
The price is $476
Dec 21 - Dec 22
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
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 Florida Keys Hotel Reviews

Find out more about Lower Florida Keys

Lower Florida Keys Cottages information

Number of reviews
1,560
Accommodation
109 Cottages
Lowest Price
$271
Highest Price
$759

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