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

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  3.  USA

  4.  Florida
  5.  Key West
  6.  Historic Seaport

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1736 Best Vacation Rentals in Historic Seaport (Starting from $191)

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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Citrus Queen at Custom House Inn | Ideal Location
Citrus Queen at Custom House Inn | Ideal Location
Apartment
Key Wets, FL, 33040, United States
0.1k from Historic Seaport center

AC, Internet, Microwave, No Smoking, TV

1 Bedroom4 Guests
9.8

Exceptional

13 reviews

$573
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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Custom House Inn | 8 BR Suite Compound on Duval!
Custom House Inn | 8 BR Suite Compound on Duval!
House
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Internet, Kitchen, Microwave, No Smoking, TV

8 Bedrooms25 Guests
10.0

Exceptional

1 reviews

$2532
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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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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The Garden House
The Garden House
House
Key West, FL, USA
0.1k from Historic Seaport center

B&bs, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
8.8

Fabulous

370 reviews

$191
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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Commodore's Cove
Commodore's Cove
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

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

4 Bedrooms12 Guests
5.5

Review score

2 reviews

$1713
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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Seaport Suite
Seaport Suite
Apartment
Key West, FL, USA
0.1k from Historic Seaport center

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

4 Bedrooms12 Guests
New to Booking
$1517
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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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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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 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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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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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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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
Check Availability
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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Commodore's Compound - One block from Duval St
Commodore's Compound - One block from Duval St
Apartment
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

8 Bedrooms24 Guests
9.0

Fabulous

12 reviews

$3236
Average price / night
Check Availability
Seaport Suite - Steps from Duval Street
Seaport Suite - Steps from Duval Street
Apartment
Key West, FL, 33040, United States
0.1k from Historic Seaport center

AC, Balcony, Dryer, Extra Bed, Hot Tub, Internet, Kitchen, Laundry, Microwave

4 Bedrooms12 Guests
8.6

Fabulous

12 reviews

$1661
Average price / night
Check Availability
Commodore's Cove - One block from Duval St
Commodore's Cove - One block from Duval St
Apartment
Key West, FL, 33040, United States
0.1k from Historic Seaport center

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

4 Bedrooms12 Guests
8.8

Fabulous

20 reviews

$1600
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 in Historic Seaport.

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Frequently Asked Questions

You can explore 1736 verified vacation rentals in Historic Seaport. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Historic Seaport vary depending on the season, property size, and location. Rates typically start from around $191 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Historic Seaport include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Historic Seaport welcome pets. Currently, 37 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Historic Seaport often include amenities such as Internet, Pool, and Pet Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.