Cottage Rentals in Key West Historic District, FL: Compare 10+ Sites & Save

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  5.  Key West
  6.  Key West Historic District

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64 Best Cottage Rentals in Key West Historic District (Starting from $236)

Charming pet friendly 2 bed/2 bath cottage 3 blocks from Duval
Charming pet friendly 2 bed/2 bath cottage 3 blocks from Duval
Cottage
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
New to Booking
$363
Average price / night
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CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
Cottage
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$374
Average price / night
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Old Town Key West Cottage 3bed/2bath
Old Town Key West Cottage 3bed/2bath
Cottage
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$404
Average price / night
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HIDDEN OASIS 3 blocks from Duval
HIDDEN OASIS 3 blocks from Duval
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
9.6

Exceptional

100 reviews

$764
Average price / night
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Find your zen at HIDDEN TREASURE
Find your zen at HIDDEN TREASURE
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.0

Fabulous

16 reviews

$1263
Average price / night
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Get your ISLAND STLYE on!
Get your ISLAND STLYE on!
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
9.6

Exceptional

84 reviews

$451
Average price / night
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OSPREY STUDIO @ The Colony-Sleeps up to 4
OSPREY STUDIO @ The Colony-Sleeps up to 4
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Internet, Kitchen, Microwave, No Smoking, Pool, TV

1 Bedroom4 Guests
9.4

Superb

57 reviews

$727
Average price / night
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Colony Poolside: A charming bungalow near Duval Street
Colony Poolside: A charming bungalow near Duval Street
Cottage
Key west, FL, 33040, United States
0.3k from Key West Historic District center

AC, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio, Pool

1 Bedroom2 Guests
9.6

Exceptional

154 reviews

$465
Average price / night
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COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Extra Bed, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio

1 Bedroom4 Guests
9.4

Superb

120 reviews

$468
Average price / night
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Colony Sunset- Bright and airy cottage in the heart of old town Key West
Colony Sunset- Bright and airy cottage in the heart of old town Key West
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio

1 Bedroom4 Guests
9.8

Exceptional

118 reviews

$429
Average price / night
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PINEAPPLE COTTAGE,  2BR/2BA-Pvt Pool,  1/2 block to Duval
PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

236 reviews

$998
Average price / night
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CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.8

Exceptional

179 reviews

$774
Average price / night
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Oasis in Old Town - our special home
Oasis in Old Town - our special home
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

5 Bedrooms6 Guests
9.6

Exceptional

23 reviews

$267
Average price / night
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Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$810
Average price / night
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Old Town cottage
Old Town cottage
Cottage
Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$350
Average price / night
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Eyebrow Suite - 2bd/1.5ba Suite off Duval
Eyebrow Suite - 2bd/1.5ba Suite off Duval
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Dryer, Hot Tub, Kitchen, Laundry, Microwave, No Smoking, TV, Washer

2 Bedrooms4 Guests
9.6

Exceptional

77 reviews

$601
Average price / night
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NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location
NEW! - The Jolly Rooster Cottage\nSteps to Duval - Prime and Quiet Location
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.8

Exceptional

19 reviews

$559
Average price / night
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Quaint Key West Escape Old Town - Local Living
Quaint Key West Escape Old Town - Local Living
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Heater, Laundry, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$236
Average price / night
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LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!
LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$412
Average price / night
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The Dancing Rooster: 2 Blocks from Duval in Old Town.
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Barbecue, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
9.8

Exceptional

141 reviews

$722
Average price / night
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Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
Cottage
Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$405
Average price / night
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~Hibiscus Cottage~ 18+ Adult Only cottage near Duval St
~Hibiscus Cottage~ 18+ Adult Only cottage near Duval St
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
9.8

Exceptional

16 reviews

$736
Average price / night
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~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St
~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
9.2

Superb

5 reviews

$626
Average price / night
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~GARDENIA COTTAGE~18+ Adult Only cottage near Duval St
~GARDENIA COTTAGE~18+ Adult Only cottage near Duval St
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
9.6

Exceptional

4 reviews

$655
Average price / night
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Conch Republic Consul General's Cottage.-Historic District
Conch Republic Consul General's Cottage.-Historic District
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.4

Superb

168 reviews

$386
Average price / night
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Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.2

Superb

84 reviews

$393
Average price / night
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Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Cottage
Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$513
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Cottage Rentals in Key West Historic District.

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Key West Historic District Cottage Rentals on the Map

Frequently Asked Questions

You can explore 64 verified cottage rentals in Key West Historic District. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Key West Historic District vary based on the season, location, and amenities offered. Rates typically start from around $236 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Key West Historic District feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 21 listings in Key West Historic District welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Key West Historic District are known for their comfort and charm, often including amenities such as Bedding/Linens, Kitchen, and Wellness Facilities. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Key West Historic District are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.