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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Jackson Square

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485 Best Vacation Rentals with Private Pool in Jackson Square (Starting from $145)

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
Jackson Square, Key West, Florida, USA
0.7k from Jackson Square 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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Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Apartment
Key West, FL, 33040, United States
0.0k from Jackson Square center

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

4 Bedrooms8 Guests
9.6

Exceptional

52 reviews

$1128
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 Jackson Square 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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**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
0.1k from Jackson Square 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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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
0.2k from Jackson Square 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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SUN, SEA & SKY at Truman Annex in Key West
SUN, SEA & SKY at Truman Annex in Key West
Condo
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

1 Bedroom4 Guests
9.8

Exceptional

64 reviews

$145
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
0.2k from Jackson Square 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
0.2k from Jackson Square 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
0.2k from Jackson Square 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
0.2k from Jackson Square 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
0.2k from Jackson Square 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
0.2k from Jackson Square 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 Jackson Square 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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**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

3 Bedrooms6 Guests
9.8

Exceptional

38 reviews

$458
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
0.2k from Jackson Square 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
0.2k from Jackson Square 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
0.2k from Jackson Square 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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Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$215
Average price / night
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Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Month Long Stays Only
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Month Long Stays Only
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

3 Bedrooms8 Guests
10.0

Exceptional

37 reviews

$795
Average price / night
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Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms8 Guests
9.4

Superb

50 reviews

$963
Average price / night
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A Wave From It All at The Truman Annex in Key West
A Wave From It All at The Truman Annex in Key West
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$750
Average price / night
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Tropical Oasis in the Truman Annex with a private pool
Tropical Oasis in the Truman Annex with a private pool
House
Key West, FL, 33040, United States
0.2k from Jackson Square center

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

2 Bedrooms6 Guests
10.0

Exceptional

36 reviews

$641
Average price / night
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3 Bedroom Key West Home - Perfect Location & Private Pool
3 Bedroom Key West Home - Perfect Location & Private Pool
House
Key West, FL, 33040, United States
0.3k from Jackson Square center

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

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$1394
Average price / night
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**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.3k from Jackson Square center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$573
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
0.3k from Jackson Square 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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**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
0.3k from Jackson Square 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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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
0.3k from Jackson Square 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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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 Jackson Square.

Where to stay in Jackson Square? Best neighborhoods & areas

Jackson Square Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Jackson Square vary depending on the property size, location, and travel season. Rates typically start from around $145 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 Jackson Square also welcome pets. Currently, 14 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 Jackson Square 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 Jackson Square 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.