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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Key Haven cottages

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, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Property grounds
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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!
Exterior
Private Oceanfront Cottage with 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 21 - Dec 22
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior
Cottage with swimming pool and 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!
Outdoor dining
Living Life Dockside

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
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)
"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!
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.
$312 nightly
The price is $346
Dec 21 - Dec 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, a heated pool
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
8.6 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 21 - Dec 22
Total with taxes and fees
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.
$297 nightly
The price is $330
Dec 21 - Dec 22
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
Terrace/patio
OSPREY STUDIO @ The Colony-Sleeps up to 4

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.
$636 nightly
The price is $697
Dec 24 - Dec 25
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4
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)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
$678 nightly
The price is $752
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Property grounds
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, (26)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Osprey Suite | Charming Hideaway, 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, (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!
Property grounds
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.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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
$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!
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.
$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!
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.
$896 nightly
The price is $985
Dec 24 - Dec 25
Total with taxes and fees
Find your zen at HIDDEN TREASURE
Outdoor dining
HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (95)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
United States
Kathryn W.
$973 nightly
The price is $1,072
Jan 17 - Jan 18, 2026
Total with taxes and fees
HIDDEN OASIS 3 blocks 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 Key Haven Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"The front desk staff was amazing. The hotel is clean and in a wonderful location. They offer a free shuttle to the main area near Duval Street which is super convenient. We would definitely stay here again. Oh and we were here celebrating my birthday and they left us a bottle of champagne and a cute card in our room, it totally made my day. "
JULIE 4-night trip
Posted 18 hours ago
Hilton Garden Inn Key West / The Keys Collection

Find out more about Key Haven

Key Haven Cottages information

Number of reviews
954
Accommodation
114 Cottages
Lowest Price
$285
Highest Price
$1,072

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