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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Key West Historic District

Refine your search

Price per night

Amenity Filter

Rating

1736 Best Vacation 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
~ 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
Check Availability
~ 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
Check Availability
~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
Check Availability
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
Check Availability
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
Check Availability
~ 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
Check Availability
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
Check Availability
New Listing-  Modern & spacious historic home with private pool and parking
New Listing- Modern & spacious historic home with private pool and parking
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$531
Average price / night
Check Availability

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 Vacation Rentals in Key West Historic District.

Where to stay in Key West Historic District? Best neighborhoods & areas

Stay Near Key West Historic District's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Key West Historic District Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1736 verified vacation rentals in Key West Historic District. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Key West Historic District vary depending on the season, property size, and location. Rates typically start from around $156 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Key West Historic District include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Key West Historic District welcome pets. Currently, 40 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Key West Historic District often include amenities such as Internet, Pool, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.