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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Historic Seaport

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1053 Best Oceanfront Rentals in Historic Seaport (Starting from $306)

Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.2k from Historic Seaport center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms26 Guests
8.4

Very Good

299 reviews

$345
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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Galleon Resort and Marina
Galleon Resort and Marina
Resort
Historic Seaport, Key West, Florida, USA
0.3k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Beach, Jacuzzis, Places to stay

84 Bedrooms20 Guests
7.1

Good

111 reviews

$603
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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Hyatt Centric Key West Resort & Spa
Hyatt Centric Key West Resort & Spa
Resort
Key West, FL, USA
0.3k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

118 Bedrooms30 Guests
8.2

Very Good

545 reviews

$387
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 Island Suite at KW Vacation
The Island Suite at KW Vacation
Apartment
Key West, FL, USA
0.3k from Historic Seaport center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
9.6

Exceptional

36 reviews

$395
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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Westwinds Inn
Westwinds Inn
House
Key West, FL, USA
0.4k from Historic Seaport center

B&bs, Accommodations, Pools, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals, Places to stay

27 Bedrooms28 Guests
8.8

Fabulous

732 reviews

$475
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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Pier House Resort & Spa
Pier House Resort & Spa
Resort
Key West, FL, USA
0.4k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

140 Bedrooms62 Guests
8.3

Very Good

664 reviews

$534
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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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.4k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

12 Bedrooms31 Guests
8.3

Very Good

54 reviews

$306
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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Opal Key Resort & Marina
Opal Key Resort & Marina
Resort
Key West, FL, USA
0.5k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs

188 Bedrooms106 Guests
8.6

Fabulous

1178 reviews

$716
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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Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort
Resort
Key West, FL, USA
0.5k from Historic Seaport center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, 4-star, Lodgings, Jacuzzis

97 Bedrooms46 Guests
8.7

Fabulous

116 reviews

$578
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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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.6k from Historic Seaport center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
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
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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
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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
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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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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
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 Oceanfront Rentals in Historic Seaport.

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Historic Seaport Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Historic Seaport. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Historic Seaport vary depending on the property size, exact beachfront location, and season. Rates typically start from around $306 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Historic Seaport offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Historic Seaport welcome pets. Currently, 31 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Historic Seaport often include features designed for a comfortable coastal stay, such as Ocean View, Oceanfront, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.