Short-Term 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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2250 Best Short-Term Rentals in Key West Historic District (Starting from $156)

Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays
Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays
House
Key West, FL, USA
0.0k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$248
Average price / night
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Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
House
Key West, FL, 33040, United States
0.0k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$574
Average price / night
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Casa Azul-Open Concept Home With Pool
Casa Azul-Open Concept Home With Pool
House
Key West, FL, USA
0.1k from Key West Historic District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$343
Average price / night
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little bodega in Key West
little bodega in Key West
House
Key West, FL, 33040, United States
0.0k from Key West Historic District center

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

1 Bedroom3 Guests
9.6

Exceptional

4 reviews

$484
Average price / night
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Midnight Cowboy by AvantStay 3 Artistic Spaces
Midnight Cowboy by AvantStay 3 Artistic Spaces
House
Key West, FL, USA
0.1k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$406
Average price / night
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Truman House - Private Pool Home in the Heart of Old Town Key West!
Truman House - Private Pool Home in the Heart of Old Town Key West!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.4

Superb

9 reviews

$1391
Average price / night
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Tennessee Williams by AvantStay Funky Design Pool
Tennessee Williams by AvantStay Funky Design Pool
House
Key West, FL, USA
0.1k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$269
Average price / night
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Escape to \"Casa Escondida\"
Escape to \"Casa Escondida\"
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

2 Bedrooms4 Guests
New to Booking
$474
Average price / night
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Casa Del Sol
Casa Del Sol
House
Key West, FL, USA
0.1k from Key West Historic District center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$393
Average price / night
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Charming 2-bedroom House in Historic Key West with Pool
Charming 2-bedroom House in Historic Key West with Pool
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

2 Bedrooms4 Guests
New to Booking
$209
Average price / night
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Green Mermaid
Green Mermaid
House
Key West, FL, USA
0.1k from Key West Historic District center

Air Conditioner, Pet Friendly, Laundry, Hot Tub, Internet, Child Friendly

2 Bedrooms4 Guests
New to Booking
$238
Average price / night
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Chic 1BR wonderful porches, heart of Old Town Key West. Total renovation.
Chic 1BR wonderful porches, heart of Old Town Key West. Total renovation.
Apartment
KEY WEST, FL, 33040, United States
0.1k from Key West Historic District center

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

1 Bedroom2 Guests
8.0

Good

1 reviews

$156
Average price / night
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Passover Cottage
Passover Cottage
House
Key West, FL, USA
0.2k from Key West Historic District center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$980
Average price / night
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Windsor Blue Private Pool and Off Street Parking
Windsor Blue Private Pool and Off Street Parking
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, TV, Washer

2 Bedrooms4 Guests
New to Booking
$363
Average price / night
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NUMBER ELEVEN at Scarlet Mango Inn Key West
NUMBER ELEVEN at Scarlet Mango Inn Key West
House
Key West, FL, USA
0.2k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$524
Average price / night
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The Kaleidoscope House - A Colorful Key West Hideaway w Pool & Jacuzzi
The Kaleidoscope House - A Colorful Key West Hideaway w Pool & Jacuzzi
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Hot Tub, Internet, Living Area, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$424
Average price / night
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GOLDEN NUGGET at Scarlet Mango Inn Key West
GOLDEN NUGGET at Scarlet Mango Inn Key West
House
Key West, FL, USA
0.2k from Key West Historic District center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$395
Average price / night
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Bohemian island home full of color and modern amenities - in a great location
Bohemian island home full of color and modern amenities - in a great location
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

2 Bedrooms6 Guests
New to Booking
$315
Average price / night
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JULIE at Scarlet Mango Inn Key West
JULIE at Scarlet Mango Inn Key West
House
Key West, FL, USA
0.2k from Key West Historic District center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$417
Average price / night
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~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$646
Average price / night
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~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

1 Bedroom3 Guests
9.6

Exceptional

158 reviews

$421
Average price / night
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~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

1 Bedroom3 Guests
9.6

Exceptional

175 reviews

$397
Average price / night
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Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$916
Average price / night
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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$431
Average price / night
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~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$361
Average price / night
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QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

3 Bedrooms6 Guests
8.4

Very Good

10 reviews

$420
Average price / night
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Old Town! Spacious Condo in Historic Home w/Pool!
Old Town! Spacious Condo in Historic Home w/Pool!
Condo
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.4

Superb

10 reviews

$316
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 Short-Term Rentals in Key West Historic District.

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Key West Historic District Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2250 verified short-term rentals in Key West Historic District, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Key West Historic District vary depending on location, property size, and travel dates. Rates typically start from around $156 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Key West Historic District include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Key West Historic District, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Key West Historic District often include amenities such as Internet, Pool, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Key West Historic District are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.