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

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  2. Vacation Rentals with Private Pool
  3.  USA

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

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485 Best Vacation Rentals with Private Pool in Key West Historic District (Starting from $247)

Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
House
Key West Historic District, Key West, Florida, USA
0.2k from Key West Historic District center

Pool, Private Pool, Kitchen, Parking, Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$348
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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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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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 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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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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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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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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LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
House
Key West, FL, 33040, United States
0.1k from Key West Historic District center

AC, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$350
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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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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CONCH EASY LIVING -1 block to Duval-Monthly rental
CONCH EASY LIVING -1 block to Duval-Monthly rental
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
New to Booking
$347
Average price / night
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KNOT A WORRY so close to Duval at this monthly rental
KNOT A WORRY so close to Duval at this monthly rental
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

2 Bedrooms6 Guests
New to Booking
$336
Average price / night
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COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West
COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$247
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
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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
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Elizabeth Retreat: A three bedroom historic home in Old Town
Elizabeth Retreat: A three bedroom historic home in Old Town
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms6 Guests
9.2

Superb

10 reviews

$319
Average price / night
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~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
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

178 reviews

$1649
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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LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms8 Guests
10.0

Exceptional

223 reviews

$1219
Average price / night
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~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

3 Bedrooms6 Guests
10.0

Exceptional

139 reviews

$1315
Average price / night
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~QUEEN CONCH ~ Amazing location with pool and room for family and friends!
~QUEEN CONCH ~ Amazing location with pool and room for family and friends!
House
Key West, FL, 33040, United States
0.2k from Key West Historic District center

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

4 Bedrooms14 Guests
10.0

Exceptional

50 reviews

$2051
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 with Private Pool in Key West Historic District.

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Key West Historic District Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Key West Historic District. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Key West Historic District vary depending on the property size, location, and travel season. Rates typically start from around $247 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Key West Historic District also welcome pets. Currently, 16 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Key West Historic District often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Key West Historic District include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.