This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Private Homes, Historic Seaport Vacation Rentals Show this location only Back to top
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Key West Boat & Breakfast, Reef Sailing Trips, Asa Sailing Coming Soon
2BR/2BA
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Sleeps 4
– Private Homes, Historic Seaport #169864
$320 - $375 per night 2-3 night min stay
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Mojitoville: Pet-Friendly Old Town Cottage with Private Pool
3BR+/2BA
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Sleeps 6-7
– Private Homes, Historic Seaport #54945
$4000- $7000/mo
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Private Yacht 3 Blocks from Duval Street & Sloppy Joe's
3BR/3BA
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Sleeps 6
– Private Homes, Historic Seaport #390580
$595 - $650 per night 2-5 night min stay
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Classic Key West Estate ~ Spectacular Historic Seaport Home
7BR+/5BA
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Sleeps 16-18
– Private Homes, Historic Seaport #138048
$1150-$1450nt - $5200-$7700/wk
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The Grand Marshal Key West - a Rare One-of-a-Kind Estate Home
5BR+/4BA
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Sleeps 10-14
– Private Homes, Historic Seaport #139521
$1050-$1375/nt - $5000-$6900/wk
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Stop! Paradise Calling! Boat Slip, Heated Pool, Close to All
2BR+/2BA
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Sleeps 6-8
– Private Homes, Historic Seaport #400038
From $1,575/wk to $3,300/wk
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Historic Seaport Home
4BR+/4.5BA
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Sleeps 10
– Private Homes, Historic Seaport #120234
$7,500- $15,000/mo
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Sawyer's Escape
3BR/0BA
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Sleeps 6
– Private Homes, Historic Seaport #459582
$6500 per month 28 night min stay
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Seaport Suite, Perfect Downtown Location, Walk Everywhere!
4BR+/2BA
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Sleeps 8-10
– Private Homes, Historic Seaport #324984
$348- $445/nt
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Tropical Tranquility - 5 Star Caribbean Resort-Style Villa
4BR/3.5BA
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Sleeps 8
– Private Homes, Historic Seaport #173086
$950-$1250/nt - $4500-$6000/wk
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Monthly Rental: Historic Oasis Steps from Key West's Best Attractions
3BR/2BA
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Sleeps 6
– Private Homes, Historic Seaport #449146
monthly rental 7,000.00-10,000.00
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Island Village Cottage-Historic Seaport of Key West
2BR+/2BA
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Sleeps 4-6
– Private Homes, Historic Seaport #183984
$325-$400/nt - $1850-$2550/wk
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Key West Historic Seaport Tree Houseefficiency with Deck
1BR+/1BA
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Sleeps 3
– Private Homes, Historic Seaport #397437
$3000/mo
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Summertime Special 10% Off June-September!
2BR/1BA
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Sleeps 2-4
– Private Homes, Historic Seaport #440909
$4480 per month 28 night min stay
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Charming Old Town Cottage for Single or Couple
1BR/1BA
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Sleeps 2
– Private Homes, Historic Seaport #384413
$3500 high season Feb., March, April
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Writer's Personal Residence in Old Town
2BR/1.5BA
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Sleeps 4
– Private Homes, Historic Seaport #381042
$7000.00/mo
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Key West Boat & Breakfast, Reef Sailing Trips, Asa Sailing Coming Soon
2BR/2BA
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Sleeps 4
– Private Homes, Historic Seaport #169864
Overview of Private Homes, Historic Seaport Vacation Rentals
Enjoy Historic Seaport House Rentals for a Taste of Old Key West
The Key West waterfront on the Gulf side is where the island's founding citizens of the late nineteenth century built the Historic Seaport community that still captivates locals and visitors alike. The homes, buildings, and shipping docks of the Key West Historic Seaport District remain a world-renowned grouping of Victorian Era/Caribbean-influenced architecture and design. Residents of Historic Seaport house rentals are lucky enough to be able to spend some leisure time immersed in the charms of a one-of-a-kind Old World Key West neighborhood that harkens back to the days of seafaring merchants.
Right in the Midst of Key West History and Modern Day Fun
Residents at Historic Seaport beach rentals can follow the Historic Seaport Harbor Walk to nearby Old Town Key West — a two mile long wooden walk that passes charter boats, sunset cruisers, tall ships, and open-air bars and restaurants. Take in lots of sea breezes, sunshine, and people-watching as you make your way to Old Town Key West and all of its distinctive attractions, including shops, art galleries, cafes, restaurants, and museums. Not far from centrally located Historic Seaport beach rentals are all the other destinations and activities popular with generations of Key West locals and visitors: tropical beaches, snorkeling, diving, water sports, golfing, marinas and boating, fishing, botanical gardens, the Key West Aquarium, and the nightly Mallory Square Sunset Celebration.
A Fascinating Key West Waterfront Neighborhood You'll Never Forget
The Historic Seaport District offers a number of Key West vacation rentals that are delightfully renovated residences, each with its own "personality" and features. Historic Seaport house rentals range from grand Caribbean-style villas to former sea merchants' homes to quaint cottages. Amenities at these house rentals may include comfortable living spaces, bedrooms, kitchens, laundry facilities, and recreational areas that welcome visitors in authentic and time-honored Key West style.