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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West

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485 Best Vacation Rentals with Private Pool in Key West (Starting from $323)

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, Florida, USA
0.6k from Key West 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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Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Villa
Key West, FL, 33040, United States
0.1k from Key West center

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

3 Bedrooms7 Guests
New to Booking
$1047
Average price / night
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Luxe Designer Oasis + Guest House steps off Duval
Luxe Designer Oasis + Guest House steps off Duval
House
Key West, FL, 33040, United States
0.1k from Key West center

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

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1050
Average price / night
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PINEAPPLE COTTAGE,  2BR/2BA-Pvt Pool,  1/2 block to Duval
PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
Cottage
Key West, FL, 33040, United States
0.1k from Key West center

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

2 Bedrooms4 Guests
10.0

Exceptional

236 reviews

$998
Average price / night
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Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
House
Key West, FL, 33040, United States
0.1k from Key West center

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

1 Bedroom6 Guests
9.4

Superb

39 reviews

$809
Average price / night
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Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
House
Key West, FL, 33040, United States
0.1k from Key West center

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

4 Bedrooms8 Guests
9.2

Superb

53 reviews

$1196
Average price / night
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Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
House
Key West, FL, 33040, United States
0.1k from Key West center

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

4 Bedrooms10 Guests
8.8

Fabulous

44 reviews

$1394
Average price / night
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THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
House
Key West, FL, 33040, United States
0.1k from Key West center

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

2 Bedrooms6 Guests
7.0

Good

4 reviews

$323
Average price / night
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Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
House
Key West, FL, 33040, United States
0.1k from Key West center

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

6 Bedrooms14 Guests
9.6

Exceptional

10 reviews

$2253
Average price / night
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Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Villa
Key West, FL, 33040, United States
0.1k from Key West center

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

3 Bedrooms8 Guests
9.8

Exceptional

174 reviews

$1100
Average price / night
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Location In Down Town Key West W/ 2 Pools,  Huge Private Roof Deck & Parking
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Villa
key west, FL, 33040, United States
0.1k from Key West center

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

6 Bedrooms16 Guests
9.8

Exceptional

78 reviews

$2064
Average price / night
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Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
House
Key West, FL, 33040, United States
0.1k from Key West center

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

3 Bedrooms8 Guests
9.8

Exceptional

158 reviews

$822
Average price / night
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~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
House
Key West, FL, 33040, United States
0.1k from Key West center

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

3 Bedrooms7 Guests
10.0

Exceptional

193 reviews

$1689
Average price / night
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BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
House
Key West, FL, 33040, United States
0.1k from Key West center

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

3 Bedrooms8 Guests
9.8

Exceptional

104 reviews

$1422
Average price / night
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No secrets at Pilar's Secret - Just a great location!
No secrets at Pilar's Secret - Just a great location!
House
Key West, FL, 33040, United States
0.2k from Key West center

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

3 Bedrooms8 Guests
9.8

Exceptional

116 reviews

$1487
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 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 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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**BLUE HERON'S HIDEOUT @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVI
**BLUE HERON'S HIDEOUT @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVI
House
Key West, FL, 33040, United States
0.2k from Key West center

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

4 Bedrooms8 Guests
New to Booking
$487
Average price / night
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**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Key West center

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

3 Bedrooms7 Guests
New to Booking
$643
Average price / night
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Luxury Residence in Old Town Key West w Pool
Luxury Residence in Old Town Key West w Pool
House
Key West, FL, 33040, United States
0.2k from Key West center

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

4 Bedrooms10 Guests
New to Booking
$563
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 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 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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**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Key West center

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

5 Bedrooms10 Guests
10.0

Exceptional

152 reviews

$1564
Average price / night
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**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from Key West center

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

6 Bedrooms12 Guests
9.8

Exceptional

95 reviews

$1921
Average price / night
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**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Key West center

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

5 Bedrooms10 Guests
9.8

Exceptional

83 reviews

$1388
Average price / night
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**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Key West center

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

16 Bedrooms32 Guests
10.0

Exceptional

5 reviews

$4416
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 center

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

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$374
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.

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Key West 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. 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 vary depending on the property size, location, and travel season. Rates typically start from around $323 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 also welcome pets. Currently, 23 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 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 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.