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Islamorada
Cottages
Top Cottages in Monroe County

Old Wooden Bridge Resort and Marina
1791 Bogie Drive Big Pine Key FL
$254 nightly
The price is $286 total per night
$286 total
May 25 - May 26
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
$125 nightly
The price is $141 total per night
$141 total
May 31 - Jun 1
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

Heart of Downtown Key West Cottage With Off-Street Parking
Key West FL
Free WiFi in public areas is available at this cottage.
Kitchen
Washer

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Key West FL
This cottage features barbecue grills.
Kitchen
Pet friendly

Key Largo Waterfront Paradise w/Kayaks, Private Dock & BBQ
Key Largo FL
An outdoor pool is featured at this cottage, along with laundry facilities and barbecue grills.
Pool
Kitchen

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
An outdoor pool is featured at this cottage, along with laundry facilities and barbecue grills.
Pool
Kitchen

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Key West FL
$597 nightly
The price is $663 total per night
$663 total
Jun 14 - Jun 15
Total with taxes and fees
This cottage includes a garden and laundry facilities.
Kitchen
Washer

~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
Key West FL
Laundry facilities, concierge services, and barbecue grills are available at this cottage.
Pool
Washer

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Cudjoe Key FL
This cottage features a terrace, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
$267 nightly
The price is $296 total per night
$296 total
May 27 - May 28
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

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key FL
$386 nightly
The price is $428 total per night
$428 total
May 27 - May 28
Total with taxes and fees
This cottage features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
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
1791 Bogie Drive Big Pine Key FL
$254 nightly
The price is $286 total per night
$286 total
May 25 - May 26
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
$125 nightly
The price is $141 total per night
$141 total
May 31 - Jun 1
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

Heart of Downtown Key West Cottage With Off-Street Parking
Key West FL
Free WiFi in public areas is available at this cottage.
Kitchen
Washer

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Key West FL
This cottage features barbecue grills.
Kitchen
Pet friendly

Key Largo Waterfront Paradise w/Kayaks, Private Dock & BBQ
Key Largo FL
An outdoor pool is featured at this cottage, along with laundry facilities and barbecue grills.
Pool
Kitchen

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
An outdoor pool is featured at this cottage, along with laundry facilities and barbecue grills.
Pool
Kitchen

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Key West FL
$597 nightly
The price is $663 total per night
$663 total
Jun 14 - Jun 15
Total with taxes and fees
This cottage includes a garden and laundry facilities.
Kitchen
Washer

~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
Key West FL
Laundry facilities, concierge services, and barbecue grills are available at this cottage.
Pool
Washer

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Cudjoe Key FL
This cottage features a terrace, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
$267 nightly
The price is $296 total per night
$296 total
May 27 - May 28
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

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key FL
$386 nightly
The price is $428 total per night
$428 total
May 27 - May 28
Total with taxes and fees
This cottage features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
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

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
$259 nightly
The price is $286 total per night from Jun 21 to Jun 22
$286 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (1,438 reviews)
Monroe County Cottages essential information
Accommodation | 253 Cottages |
|---|---|
Lowest Price | $141 |
Highest Price | $663 |
Popular accommodation | Old Wooden Bridge Resort and Marina, Tropical Cottages, Heart of Downtown Key West Cottage With Off-Street Parking, The Dancing Rooster: 2 Blocks from Duval in Old Town., Key Largo Waterfront Paradise w/Kayaks, Private Dock & BBQ, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location, ~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise., Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West., Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Canal front, dockage, 2 bedroom, 2 bath, Quaint cottage, pool, dockage just minutes to Key West! |
Monroe County Cottages essential information
Accommodation | 253 Cottages |
|---|---|
Lowest Price | $141 |
Highest Price | $663 |
Popular accommodation | Old Wooden Bridge Resort and Marina, Tropical Cottages, Heart of Downtown Key West Cottage With Off-Street Parking, The Dancing Rooster: 2 Blocks from Duval in Old Town., Key Largo Waterfront Paradise w/Kayaks, Private Dock & BBQ, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location, ~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise., Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West., Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Canal front, dockage, 2 bedroom, 2 bath, Quaint cottage, pool, dockage just minutes to Key West! |
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- Vacation Homes in Dredgers Key
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- Condos in Key West
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- Extended Stay Hotels in Key West
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- Hostels in Key West
- All Inclusive Resorts & in Key West
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- Safari Camps in Flamingo
- Treehouses in Flamingo
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