A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.
CottagesCottages

Key West

Key West

Our top choices for Monroe County cottages

A floating houseboat with a covered deck and seating area, docked at a marina.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (374 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is CA $127
CA $343 total
includes taxes & fees
Oct 14 - Oct 15
Old Wooden Bridge Resort and Marina
Two small, single-story buildings with a red and yellow exterior, each with a door and windows, and surrounded by greenery and trees.

2. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,005 reviews)
"Cute little cottage perfect for couples had an amazing stay and will definitely be back to tropical cottages again"
United States
Aaron
The price is CA $113
CA $127 total
includes taxes & fees
Oct 18 - Oct 19
Tropical Cottages
A grassy area with a view of the water and palm trees.

3. Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (209 reviews)
"Convenient location."
United States
Lisa
Direct Oceanfront Cottage-Sunrise View- #2,
A single-story house with a red exterior and white trim, number 3 on the side.

4. 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, (174 reviews)
"We had a nice stay at this property, which was clean and nicely presented. It is in a calm area by the water and has some good food options close by as well. We did use the pool on 2 days and it felt like a private pool just when we used it."
United Kingdom
Anish
Cottage with swimming pool and dockage, just minutes to Key West!
An aerial view of a residential area with houses, a swimming pool, and a beach.

5. 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, (176 reviews)
"Cute little cottage, nice and quiet area exactly as to explained I would absolutely rent here again"
United States
Daniel W.
Cottage with Pool and Dockage, just minutes to Key West
A two-story building with balconies, surrounded by lush greenery and palm trees.

6. 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, (152 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is CA $714
CA $1,177 total
includes taxes & fees
Oct 20 - Oct 21
The Dancing Rooster: 2 Blocks from Duval in Old Town.
A swimming pool with lounge chairs, palm trees, and a view of the ocean.

7. 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, (85 reviews)
"Great location and close to major attractions like key west. Quite and relaxing stay with great sunrise view. "
United States
Mark G.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
A balcony with white chairs and a table, overlooking a canal with houses and palm trees.

8. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.8 out of 10, Excellent, (190 reviews)
"Very nice property, as advertised. Great location for boating and fishing. "
United States
Lawrence L.
Canal Front home with easy Ocean access
A white house with a porch, a wooden fence, and a tree in the background.

9. Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking
Key West Historic District
10.0 out of 10, Exceptional, (173 reviews)
"Second time staying. A perfect house, host and location. Will stay again."
United States
Andrew C.
Heart of Downtown Key West Cottage With Off-Street Parking
A large house with a pool, surrounded by palm trees and a well-maintained lawn.

10. Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (169 reviews)
"Loved it all! Enjoyed the location and its proximity to lots of food and stores. And a great pool and dock!"
United States
Gary R.
Cottage with Pool and Boat Dockage just minutes to Key West!
A white house with a blue awning, surrounded by lush greenery and a white picket fence.

11. Conch Republic Consul General's Cottage.-Historic District

Conch Republic Consul General's Cottage.-Historic District
Old Town Key West
9.4 out of 10, Exceptional, (188 reviews)
Conch Republic Consul General's Cottage.-Historic District
An aerial view of a residential area with houses, a swimming pool, and a small dock.

12. 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, (157 reviews)
"This is the first time we visited and we loved it, we came for our anniversary this year and it was great, the location allows you to visit all the keys and plan Key West trips easily, we stayed at cottage #5 and it was very cozy and welcoming, it was clean, you have access to the pool using the back door and a porch using the front door, very comfortable. Our favorite part was the dock, it was so peaceful watching the sunrise and hanging out, just make sure to use LOTS of sunblock , we'll love...
United States
Mari M.
Quaint cottage, pool, dockage just minutes to Key West!
A two-story house with a balcony, surrounded by tropical vegetation.

13. **DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...

**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...
Key West Historic District
9.8 out of 10, Exceptional, (162 reviews)
"Fun location, great place to stay"
United States
Vanessa B.
**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...
A two-story building with a balcony, surrounded by lush greenery and a sandy beach.

14. 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, (102 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
A two-story house with a front porch, a small front yard, and a wooden fence.

15. Charming 1BR Cottage : Steps from Hemingway House & Old Town

Charming 1BR Cottage : Steps from Hemingway House & Old Town
Old Town Key West
Charming 1BR Cottage : Steps from Hemingway House & Old Town
A coastal property with a beach, a pier, and a pool area.

16. Oceanfront Private Cottage!

Oceanfront Private Cottage!
Matecumbe
10.0 out of 10, Exceptional, (119 reviews)
"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."
United States
Kimberlee C.
Oceanfront Private Cottage!
A coastal property with a swimming pool, palm trees, and a view of the ocean.

17. 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, (68 reviews)
"Cute cottage, comfy, clean, great heated pool, and great snorkeling spot. "
United States
Carole G.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

18. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (108 reviews)
"Exactly as shown in the pictures and as described. Appreciated the extra location for the boat trailer."
United States
Laurie C.
Canal front, dockage, 2 bedroom, 2 bath
A two-story building with balconies, surrounded by lush greenery and palm trees.

19. 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, (36 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
The price is CA $714
CA $1,177 total
includes taxes & fees
Oct 25 - Oct 26
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A patio with a grill, yellow chairs, and a table under a blue umbrella, surrounded by a wooden deck and a lattice fence.

20. HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
The price is CA $357
CA $986 total
includes taxes & fees
Oct 25 - Oct 26
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 Monroe County Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"10/10 recommend!"
Jessica 3-night trip
Posted less than an hour ago
Chesapeake Beach Resort

Find out more about Monroe County

Monroe County Cottages information

Number of reviews
2,401
Accommodation
245 Cottages
Lowest Price
CA $127
Highest Price
CA $1,177

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