Book Monroe County, FL Cottages
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Top cities with Cottages to explore in Monroe County
Islamorada
Cottages
Top Cottages in Monroe County
Old Wooden Bridge Resort and Marina
1791 Bogie Drive Big Pine Key FL
$274 nightly
The price is $308 total per night
$308 total
Jan 10 - Jan 11, 2026
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
243 61st Street Gulf Marathon FL
$135 nightly
The price is $152 total per night
$152 total
Jan 8 - Jan 9, 2026
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
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Key West FL
This cottage features barbecue grills.
Kitchen
Pet friendly
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Key West FL
$541 nightly
The price is $595 total per night
$595 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Washer
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Key West FL
$541 nightly
The price is $595 total per night
$595 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Dryer
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Key West FL
$539 nightly
The price is $593 total per night
$593 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Key West FL
$541 nightly
The price is $595 total per night
$595 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Washer
Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key FL
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Key West FL
$539 nightly
The price is $593 total per night
$593 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A hot tub is featured at this cottage, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Conch Republic Consul General's Cottage.-Historic District
Key West FL
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
$312 nightly
The price is $346 total per night
$346 total
Dec 22 - Dec 23
Total with taxes and fees
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
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.
Monroe County Cottages essential information
Accommodation | 264 Cottages |
|---|---|
Lowest Price | $152 |
Highest Price | $595 |
Popular accommodation | Old Wooden Bridge Resort and Marina, Tropical Cottages, The Dancing Rooster: 2 Blocks from Duval in Old Town., Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!, Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!, Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!, Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!, Direct Oceanfront Cottage-Sunrise View- #2,, Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!, Conch Republic Consul General's Cottage.-Historic District, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Cottage with swimming pool and dockage, just minutes to Key West! |
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