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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Historic Seaport

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485 Best Vacation Rentals with Private Pool in Historic Seaport (Starting from $348)

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
Historic Seaport, Key West, Florida, USA
0.5k from Historic Seaport 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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PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

37 reviews

$2591
Average price / night
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**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

3 Bedrooms6 Guests
New to Booking
$409
Average price / night
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**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

6 Bedrooms12 Guests
10.0

Exceptional

91 reviews

$3128
Average price / night
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Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Cottage
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$513
Average price / night
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The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
9.8

Exceptional

22 reviews

$1816
Average price / night
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SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

5 Bedrooms10 Guests
9.8

Exceptional

206 reviews

$2516
Average price / night
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STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

8 Bedrooms20 Guests
9.6

Exceptional

76 reviews

$2867
Average price / night
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Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Balcony, Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$717
Average price / night
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Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$399
Average price / night
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Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$532
Average price / night
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Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport
Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$952
Average price / night
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Kemp House - in the Historic Seaport Area Key West
Kemp House - in the Historic Seaport Area Key West
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1122
Average price / night
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**CASA AVILA @ OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
**CASA AVILA @ OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

3 Bedrooms8 Guests
New to Booking
$486
Average price / night
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Rose Key Cottage - Private Pool & Near Duval
Rose Key Cottage - Private Pool & Near Duval
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

2 Bedrooms6 Guests
5.6

Review score

4 reviews

$1929
Average price / night
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The Rigby House - Pool, One block from Duval St
The Rigby House - Pool, One block from Duval St
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

6 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$3552
Average price / night
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THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

4 Bedrooms10 Guests
New to Booking
$525
Average price / night
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New Property - Belle of Key West! Old Town 29 nt min.
New Property - Belle of Key West! Old Town 29 nt min.
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

4 Bedrooms8 Guests
New to Booking
$623
Average price / night
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THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

3 Bedrooms6 Guests
9.8

Exceptional

22 reviews

$482
Average price / night
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Casa Rosa: 4BR/4BA house, pool, near Duval
Casa Rosa: 4BR/4BA house, pool, near Duval
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

4 Bedrooms8 Guests
9.6

Exceptional

85 reviews

$911
Average price / night
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Takeover at the Grand Maloney
Takeover at the Grand Maloney
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Laundry, No Smoking

6 Bedrooms16 Guests
8.6

Fabulous

7 reviews

$3386
Average price / night
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1 Block to Duval St | Banana's Foster Guesthouse
1 Block to Duval St | Banana's Foster Guesthouse
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

AC, Balcony, Barbecue, Extra Bed, Free Parking, Internet, Kitchen, Microwave, No Smoking

7 Bedrooms19 Guests
9.8

Exceptional

7 reviews

$3421
Average price / night
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Designer Octagon House of Key West - w Private Pool - Blocks off Duval
Designer Octagon House of Key West - w Private Pool - Blocks off Duval
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

4 Bedrooms8 Guests
New to Booking
$966
Average price / night
Check Availability
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from Historic Seaport center

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

3 Bedrooms6 Guests
New to Booking
$1477
Average price / night
Check Availability
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 Historic Seaport 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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CASA MARGARITA Steps to the Historic Seaport
CASA MARGARITA Steps to the Historic Seaport
House
Key West, FL, 33040, United States
0.3k from Historic Seaport center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
9.8

Exceptional

127 reviews

$1413
Average price / night
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**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.3k from Historic Seaport center

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

3 Bedrooms8 Guests
9.8

Exceptional

57 reviews

$1247
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 Historic Seaport.

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Historic Seaport Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Historic Seaport vary depending on the property size, location, and travel season. Rates typically start from around $348 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 Historic Seaport also welcome pets. Currently, 15 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 Historic Seaport 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 Historic Seaport 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.