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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Downtown

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485 Best Vacation Rentals with Private Pool in Downtown (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
Downtown, Key West, Florida, USA
0.6k from Downtown 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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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
0.0k from Downtown 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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**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
0.0k from Downtown 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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**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES
**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES
Condo
Key West, FL, 33040, United States
0.0k from Downtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

91 reviews

$1744
Average price / night
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Casa Loca - so close to Duval 3bd/2ba private home
Casa Loca - so close to Duval 3bd/2ba private home
House
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
9.8

Exceptional

149 reviews

$1191
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 Downtown 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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**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
0.1k from Downtown 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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**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
0.1k from Downtown 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
0.1k from Downtown 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
0.1k from Downtown 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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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 Downtown 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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Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
Perfect Location, \nPrivate Heated Pool,\nPristine Luxury Home!
House
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

203 reviews

$2560
Average price / night
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**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

10 Bedrooms20 Guests
10.0

Exceptional

10 reviews

$2802
Average price / night
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**SUMMER SOLSTICE @ OLD TOWN** Unique 9BR/9.5BA Compound + LAST KEY SERVICES…
**SUMMER SOLSTICE @ OLD TOWN** Unique 9BR/9.5BA Compound + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

11 Bedrooms22 Guests
9.4

Superb

6 reviews

$2925
Average price / night
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Coconut Palm - Steps from Duval with Private Pool
Coconut Palm - Steps from Duval with Private Pool
House
Key West, FL, 33040, United States
0.1k from Downtown center

AC, Balcony, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
8.8

Fabulous

35 reviews

$1286
Average price / night
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Southern Palms - Steps to Duval with Private Pool
Southern Palms - Steps to Duval with Private Pool
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

5 Bedrooms16 Guests
9.0

Fabulous

12 reviews

$2997
Average price / night
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EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

5 Bedrooms10 Guests
9.8

Exceptional

113 reviews

$1650
Average price / night
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Contra House - Private Pool & Steps to Duval Street
Contra House - Private Pool & Steps to Duval Street
House
Naval Air Station Key West, FL, 33040, United States
0.1k from Downtown center

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

4 Bedrooms12 Guests
9.6

Exceptional

26 reviews

$1917
Average price / night
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The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
House
Key West, FL, 33040, United States
0.1k from Downtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$698
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 Downtown 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 Downtown 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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Three Duval Street Suites w parking and pool
Three Duval Street Suites w parking and pool
Condo
Key West, FL, 33040, United States
0.2k from Downtown center

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

3 Bedrooms12 Guests
New to Booking
$878
Average price / night
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**HEMINGWAY'S HAVEN @ OLD TOWN** Home & Pool + LAST KEY SERVICES…
**HEMINGWAY'S HAVEN @ OLD TOWN** Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Downtown center

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

4 Bedrooms8 Guests
New to Booking
$371
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
0.2k from Downtown 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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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 Downtown 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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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
0.2k from Downtown 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
0.2k from Downtown 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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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 Downtown.

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Downtown Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Downtown 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 Downtown also welcome pets. Currently, 22 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 Downtown 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 Downtown 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.