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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Historic Seaport

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1469 Best Vacation Rentals with Pool in Historic Seaport (Starting from $203)

Star of the Seaport by Last Key Realty
Star of the Seaport by Last Key Realty
House
Key West, FL, USA
0.0k from Historic Seaport center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms12 Guests
New to Booking
$2584
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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African Queen - Harbor Walk Hideaways
African Queen - Harbor Walk Hideaways
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
5.5

Review score

2 reviews

$273
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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Harbor Walk Hideaways
Harbor Walk Hideaways
House
Key West, FL, USA
0.1k from Historic Seaport center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms14 Guests
New to Booking
$839
Average price / night
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Cozy on Caroline - Key West Seaport
Cozy on Caroline - Key West Seaport
Apartment
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

1 Bedroom4 Guests
New to Booking
$235
Average price / night
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Pilar Cottage - Harbor Walk Hideaways
Pilar Cottage - Harbor Walk Hideaways
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

Apartments, Cheap, Accommodations, Pools, Cottages, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$273
Average price / night
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Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.
Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.
Condo
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

1 Bedroom4 Guests
New to Booking
$203
Average price / night
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Atocha Cottage - Harbor Walk Hideaways
Atocha Cottage - Harbor Walk Hideaways
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

Apartments, Accommodations, Pools, Cottages, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$383
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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Atocha Cottage by Brightwild
Atocha Cottage by Brightwild
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

Apartments, Accommodations, Pools, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms6 Guests
4.5

Review score

2 reviews

$1032
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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New Rose Retreat - Pool & Parking
New Rose Retreat - Pool & Parking
House
FL, USA
0.2k from Historic Seaport center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
New to Booking
$1180
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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New Rose Petal Petite Suite - Pool & Parking
New Rose Petal Petite Suite - Pool & Parking
Apartment
FL, USA
0.2k from Historic Seaport center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom2 Guests
7.0

Good

1 reviews

$324
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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New Coastal Rose - Bright Loft with High Ceilings
New Coastal Rose - Bright Loft with High Ceilings
Apartment
FL, USA
0.2k from Historic Seaport center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom4 Guests
7.3

Good

3 reviews

$427
Average price / night
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STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
Condo
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

4 Bedrooms10 Guests
9.8

Exceptional

114 reviews

$1050
Average price / night
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Rigby House - Brand New with Private Pool
Rigby House - Brand New with Private Pool
House
Key West, FL, USA
0.2k from Historic Seaport center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

6 Bedrooms12 Guests
New to Booking
$2937
Average price / night
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STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Condo
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

4 Bedrooms10 Guests
9.2

Superb

94 reviews

$1174
Average price / night
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Kokomo Suite by Last Key Realty
Kokomo Suite by Last Key Realty
House
Key West, FL, USA
0.2k from Historic Seaport center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$488
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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Caroline On My Mind, Newly Decorated 2 bdrm, 2 bath, Light, Bright and Airy!
Caroline On My Mind, Newly Decorated 2 bdrm, 2 bath, Light, Bright and Airy!
Condo
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$545
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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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 Pool in Historic Seaport.

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Historic Seaport Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Historic Seaport. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Historic Seaport vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $203 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Historic Seaport offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Historic Seaport welcome pets. Currently, 33 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Historic Seaport often include additional outdoor features such as Pool, Internet, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Historic Seaport offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.