Book Monroe County, FL Cottages

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Top cities with Cottages to explore in Monroe County

A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

Cottages
Islamorada

Top Cottages in Monroe County

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
$225 nightly
The price is $253 total per night
$253 total
Sep 1 - Sep 2
Total with taxes and fees
A marina and an outdoor pool are featured at this cottage. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and express check-in are also on offer.
Pool
Pet friendly
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf Marathon FL
$90 nightly
The price is $101 total per night
$101 total
Sep 2 - Sep 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this cottage. Free self parking, a garden, and a snack bar/deli are also offered.
Parking included
Restaurant
Cottage with swimming pool and dockage, just minutes to Key West!

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

Cudjoe Key FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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

Key West FL
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This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
Conch Republic Consul General's Cottage.-Historic District

Conch Republic Consul General's Cottage.-Historic District

Key West FL
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

Cudjoe Key FL
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
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 FL
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Charming cottages, dockage, pool, just minutes to Key West

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

Cudjoe Key FL
Get rates
This cottage featured laundry facilities and barbecue grills.
Pool
Kitchen
**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 FL
Get rates
A hot tub is featured at this cottage, along with free WiFi in public areas and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
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 FL
Get rates
This cottage featured laundry facilities and barbecue grills.
Pool
Kitchen
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 FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Charming 1BR Cottage : Steps from Hemingway House & Old Town

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

Key West FL
Get rates
This cottage featured laundry facilities and barbecue grills.
Don't see what you're looking for?
See all available properties in Monroe County
View all properties
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.

Top Cottages in Monroe County

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
$225 nightly
The price is $253 total per night
$253 total
Sep 1 - Sep 2
Total with taxes and fees
A marina and an outdoor pool are featured at this cottage. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and express check-in are also on offer.
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf Marathon FL
$90 nightly
The price is $101 total per night
$101 total
Sep 2 - Sep 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this cottage. Free self parking, a garden, and a snack bar/deli are also offered.
Cottage with swimming pool and dockage, just minutes to Key West!

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

Cudjoe Key FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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

Key West FL
Get rates
This cottage featured laundry facilities and barbecue grills.
Conch Republic Consul General's Cottage.-Historic District

Conch Republic Consul General's Cottage.-Historic District

Key West FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

Cudjoe Key FL
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
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 FL
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Charming cottages, dockage, pool, just minutes to Key West

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

Cudjoe Key FL
Get rates
This cottage featured laundry facilities and barbecue grills.
**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 FL
Get rates
A hot tub is featured at this cottage, along with free WiFi in public areas and laundry facilities. Barbecue grills are provided for your convenience.
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 FL
Get rates
This cottage featured laundry facilities and barbecue grills.
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 FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Charming 1BR Cottage : Steps from Hemingway House & Old Town

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

Key West FL
Get rates
This cottage featured laundry facilities and barbecue grills.
Don't see what you're looking for?
See all available properties in Monroe County
View all properties
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.

Top hotels in Monroe County

Havana Cabana at Key West

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Sep 8 to Sep 9
$225 total
Sep 8 - Sep 9
Total with taxes and fees
9/10 Wonderful! (1,866 reviews)

Monroe County Cottages essential information

Accommodation
247 Cottages
Lowest Price
$101
Highest Price
$317
Popular accommodation
Old Wooden Bridge Resort and Marina, Tropical Cottages, Cottage with swimming pool and dockage, just minutes to Key West!, The Dancing Rooster: 2 Blocks from Duval in Old Town., Conch Republic Consul General's Cottage.-Historic District, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Charming cottages, dockage, pool, just minutes to Key West, **DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service..., 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, Charming 1BR Cottage : Steps from Hemingway House & Old Town

Monroe County Cottages essential information

Accommodation
247 Cottages
Lowest Price
$101
Highest Price
$317
Popular accommodation
Old Wooden Bridge Resort and Marina, Tropical Cottages, Cottage with swimming pool and dockage, just minutes to Key West!, The Dancing Rooster: 2 Blocks from Duval in Old Town., Conch Republic Consul General's Cottage.-Historic District, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Charming cottages, dockage, pool, just minutes to Key West, **DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service..., 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, Charming 1BR Cottage : Steps from Hemingway House & Old Town

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