Search Rockland Key Cottages

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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Rockland Key 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, (50)
"Great area. Quiet and comfortable "
United States
nancy c.
$286 nightly
The price is $317
Dec 17 - Dec 18
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 17 - Dec 18
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
Outdoor dining
Canal front, dockage, 2 bedroom, 2 bath

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 17 - Dec 18
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
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.
$355 nightly
The price is $390
Dec 20 - Dec 21
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from 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
8.6 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.
$286 nightly
The price is $317
Dec 17 - Dec 18
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.
$286 nightly
The price is $317
Dec 17 - Dec 18
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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
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 17 - Dec 18
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (52)
"Check in was easy, place nice & quiet. Kitchen facilities was good. Had a problem with the microwave, property manager took care of it within hours. WiFi great. Access was easy once you got used to it."
United States
myra c.
$411 nightly
The price is $456
Dec 26 - Dec 27
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.
$618 nightly
The price is $686
Dec 19 - Dec 20
Total with taxes and fees
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
Quaint cottage, pool, dockage just minutes to 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, (146)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$429 nightly
The price is $476
Dec 26 - Dec 27
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!
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.
$342 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to 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.
$346 nightly
The price is $380
Dec 18 - Dec 19
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
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.
$690 nightly
The price is $766
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.
$342 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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.
$920 nightly
The price is $1,011
Dec 24 - Dec 25
Total with taxes and fees
Find your zen at HIDDEN TREASURE
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.
$342 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
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
$478 nightly
The price is $526
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ibis Suite | Bright Hideaway, 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 Rockland Key Hotel Reviews

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Absolutely wonderful stay! The property and the room were beautiful! The staff was so helpful and welcoming. Highly recommend this property! "
Julianna 4-night trip
Posted 9 hours ago
Parrot Key Hotel & Villas

Find out more about Rockland Key

Rockland Key Cottages information

Number of reviews
942
Accommodation
114 Cottages
Lowest Price
$317
Highest Price
$1,011

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