Vacation Rentals with Private Pool in Key West Art and Historical Society, 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 Art and Historical Society

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485 Best Vacation Rentals with Private Pool in Key West Art and Historical Society (Starting from $216)

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 Art and Historical Society, Key West, Florida, USA
4.2k from Key West Art and Historical Society 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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Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.
Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.
House
Key West, FL, 33040, United States
1.2k from Key West Art and Historical Society center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Laundry, Pool, TV

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$578
Average price / night
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RISE AND SHINE ~ Canal Front 3 BR/3Ba Home w/ Heated Pool!
RISE AND SHINE ~ Canal Front 3 BR/3Ba Home w/ Heated Pool!
House
key west, FL, 33040, United States
1.2k from Key West Art and Historical Society center

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

3 Bedrooms8 Guests
New to Booking
$412
Average price / night
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SERENITY ON SUNRISE ~  5 BR/5.5 Bath New Town Home w/ Pool & Dockage!
SERENITY ON SUNRISE ~ 5 BR/5.5 Bath New Town Home w/ Pool & Dockage!
House
Key West, FL, 33040, United States
1.3k from Key West Art and Historical Society center

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

5 Bedrooms12 Guests
New to Booking
$654
Average price / night
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Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
House
Key West, FL, 33040, United States
1.4k from Key West Art and Historical Society center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
9.4

Superb

9 reviews

$524
Average price / night
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OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
House
Key West, FL, 33040, United States
1.4k from Key West Art and Historical Society center

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

5 Bedrooms14 Guests
9.8

Exceptional

7 reviews

$449
Average price / night
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Key West Lush Tropical Canal front Retreat 3BR Private Pool, Bring Boat & Pet
Key West Lush Tropical Canal front Retreat 3BR Private Pool, Bring Boat & Pet
House
Key West, FL, 33040, United States
1.5k from Key West Art and Historical Society center

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

3 Bedrooms6 Guests
New to Booking
$454
Average price / night
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Seaside Condo, DECEMBER SPECIAL
Seaside Condo, DECEMBER SPECIAL
Condo
Key West, FL, 33040, United States
1.5k from Key West Art and Historical Society center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom2 Guests
9.4

Superb

11 reviews

$216
Average price / night
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Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
House
Key West, FL, 33040, United States
1.5k from Key West Art and Historical Society center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
9.6

Exceptional

4 reviews

$565
Average price / night
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Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!
Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!
House
Key West, FL, 33040, United States
1.7k from Key West Art and Historical Society center

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

3 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$220
Average price / night
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Rare for KW, Beautiful 3-bedroom house on Swimmable Water + Pool
Rare for KW, Beautiful 3-bedroom house on Swimmable Water + Pool
House
Stock Island, FL, 33040, United States
1.8k from Key West Art and Historical Society center

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

3 Bedrooms8 Guests
New to Booking
$534
Average price / night
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**Welcome To Poseidon's Paradise** Midtown Home & Incredible Pool *28 Nights Min
**Welcome To Poseidon's Paradise** Midtown Home & Incredible Pool *28 Nights Min
House
Key West, FL, 33040, United States
1.8k from Key West Art and Historical Society center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$460
Average price / night
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Margarita Villa-3 bedroom 3 bath home in prime location w/backyard pool oasis
Margarita Villa-3 bedroom 3 bath home in prime location w/backyard pool oasis
House
Key West, FL, 33040, United States
1.9k from Key West Art and Historical Society center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$303
Average price / night
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**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
1.9k from Key West Art and Historical Society center

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

4 Bedrooms11 Guests
New to Booking
$676
Average price / night
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Flagler's Oasis by AvantStay | Private Pool in Key West | Month Long Stays Only
Flagler's Oasis by AvantStay | Private Pool in Key West | Month Long Stays Only
House
Key West, FL, 33040, United States
1.9k from Key West Art and Historical Society center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
8.8

Fabulous

3 reviews

$279
Average price / night
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BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
House
Key West, FL, 33040, United States
2.1k from Key West Art and Historical Society center

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

2 Bedrooms4 Guests
9.6

Exceptional

15 reviews

$302
Average price / night
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Spacious Ocean Front Resort - 3 Bedroom Condo
Spacious Ocean Front Resort - 3 Bedroom Condo
Condo
Key West, FL, 33040, United States
2.2k from Key West Art and Historical Society center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
9.2

Superb

189 reviews

$909
Average price / night
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Tom's Spectacular OceanFront 3 Bdrm  Endless Atlantic view, Key West Amazing
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Condo
Key West, FL, 33040, United States
2.2k from Key West Art and Historical Society center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

139 reviews

$940
Average price / night
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Luxury High End, 2 Bikes,  Highspeed Wi-Fi, Work station,  Pool, Hot Tub, Gym
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Condo
Key West, FL, 33040, United States
2.3k from Key West Art and Historical Society center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.8

Exceptional

311 reviews

$490
Average price / night
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**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
2.3k from Key West Art and Historical Society center

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

8 Bedrooms16 Guests
10.0

Exceptional

65 reviews

$2057
Average price / night
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Private Paradise with Heated Waterfall Pool
Private Paradise with Heated Waterfall Pool
House
Key West, FL, 33040, United States
2.3k from Key West Art and Historical Society center

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

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$319
Average price / night
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**BEAUTY OF THE BEACH** Monthly Beach House Rental + LAST KEY SERVICES…
**BEAUTY OF THE BEACH** Monthly Beach House Rental + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
2.3k from Key West Art and Historical Society center

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

6 Bedrooms12 Guests
New to Booking
$594
Average price / night
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Sleep 16 guests over two side-by-side homes in exclusive Key Cove Landings
Sleep 16 guests over two side-by-side homes in exclusive Key Cove Landings
House
Key West, FL, 33040, United States
2.4k from Key West Art and Historical Society center

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

8 Bedrooms16 Guests
New to Booking
$2576
Average price / night
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Oceanview home with private pool & lush landscaping!
Oceanview home with private pool & lush landscaping!
House
Key West, FL, 33040, United States
2.4k from Key West Art and Historical Society center

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

4 Bedrooms8 Guests
9.6

Exceptional

128 reviews

$1191
Average price / night
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Spacious Waterfront 4 Bedroom Home
Spacious Waterfront 4 Bedroom Home
House
Key West, FL, 33040, United States
2.4k from Key West Art and Historical Society center

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

4 Bedrooms8 Guests
9.6

Exceptional

92 reviews

$1402
Average price / night
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Modern Waterfront Luxury Home with Heated Pool!
Modern Waterfront Luxury Home with Heated Pool!
House
Key West, FL, 33040, United States
2.4k from Key West Art and Historical Society center

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

4 Bedrooms8 Guests
9.6

Exceptional

105 reviews

$1351
Average price / night
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Waterfront Home in Key Cove Landings
Waterfront Home in Key Cove Landings
House
Key West, FL, 33040, United States
2.4k from Key West Art and Historical Society center

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

4 Bedrooms8 Guests
9.8

Exceptional

108 reviews

$1185
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 Vacation Rentals with Private Pool in Key West Art and Historical Society.

Where to stay in Key West Art and Historical Society? Best neighborhoods & areas

Key West Art and Historical Society 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 Art and Historical Society. 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 Art and Historical Society vary depending on the property size, location, and travel season. Rates typically start from around $216 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 Art and Historical Society also welcome pets. Currently, 34 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 Art and Historical Society 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 Art and Historical Society 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.