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

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  4.  Florida

  5.  Key West
  6.  Key West Historic District

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1025 Beach Home Rentals in Key West Historic District (Starting from $209)

Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Key West Historic District, Key West, Florida, USA
0.2k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Romantic, Pet-friendly, Lodgings

18 Bedrooms72 Guests
8.8

Fabulous

1291 reviews

$738
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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Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.3k from Key West Historic District center

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

3 Bedrooms6 Guests
New to Booking
$1628
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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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.3k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
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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The Island Suite at KW Vacation
The Island Suite at KW Vacation
Apartment
Key West, FL, USA
0.3k from Key West Historic District center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
9.6

Exceptional

36 reviews

$395
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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Westwinds Inn
Westwinds Inn
House
Key West, FL, USA
0.4k from Key West Historic District center

B&bs, Accommodations, Pools, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals, Places to stay

27 Bedrooms28 Guests
8.8

Fabulous

732 reviews

$475
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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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Key West Historic District, Key West, Florida, USA
0.4k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Hot tubs

13 Bedrooms28 Guests
8.8

Fabulous

193 reviews

$575
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 Garden Villas
Old Town Garden Villas
House
Key West Historic District, Key West, Florida, USA
0.5k from Key West Historic District center

View, Internet, Pool, Air Conditioner, Ocean View, Child Friendly

2 Bedrooms8 Guests
9.5

Superb

19 reviews

$258
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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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.5k from Key West Historic District center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

12 Bedrooms31 Guests
8.3

Very Good

54 reviews

$306
Average price / night
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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
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Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.5k from Key West Historic District center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms26 Guests
8.4

Very Good

299 reviews

$345
Average price / night
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Quilted Giraffe - Private Home in Old Town Key West
Quilted Giraffe - Private Home in Old Town Key West
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$814
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.6k from Key West Historic District center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Places to stay

16 Bedrooms4 Guests
8.2

Very Good

255 reviews

$514
Average price / night
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Casa Azul - Private Pool
Casa Azul - Private Pool
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

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

2 Bedrooms4 Guests
New to Booking
$382
Average price / night
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Winter Months Open Frogmore on Fleming in Downtown Key West
Winter Months Open Frogmore on Fleming in Downtown Key West
Apartment
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$426
Average price / night
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Old Town 3/3 Home, Private Heated Pool, Free Parking, Outdoor Dining, Balconies
Old Town 3/3 Home, Private Heated Pool, Free Parking, Outdoor Dining, Balconies
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms8 Guests
New to Booking
$409
Average price / night
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WINDWARD SOUTH- Delightful 2-bedroom house with Pool in Old Town Key West
WINDWARD SOUTH- Delightful 2-bedroom house with Pool in Old Town Key West
House
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
New to Booking
$607
Average price / night
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STAINED GLASS SANCTUARY ~ 3 BR/1.5 Ba Home w/ Pool and Parking!
STAINED GLASS SANCTUARY ~ 3 BR/1.5 Ba Home w/ Pool and Parking!
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms6 Guests
New to Booking
$370
Average price / night
Check Availability
Secret Villa I @ Old Town with Private Pool, close to Duval!
Secret Villa I @ Old Town with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms6 Guests
10.0

Exceptional

175 reviews

$1293
Average price / night
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Secret Villa II @ Old Town: with Private Pool, close to Duval!
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Villa
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms6 Guests
10.0

Exceptional

157 reviews

$1265
Average price / night
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**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$545
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 Beach 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

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Key West Historic District Beach Rentals on the Map

Frequently Asked Questions

You can explore 1025 verified beach rentals in Key West Historic District. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Key West Historic District vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $209 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Key West Historic District offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Key West Historic District welcome pets. Currently, 25 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Key West Historic District often include amenities designed for coastal living, such as View, Ocean View, and Pool. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.