Owner Direct Vacation
Rentals in Historic Seaport
The Best Owner Direct Vacation Rentals in Historic Seaport. Explore thousands of vacation home rentals, large cabins, and villas near Historic Seaport
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Explore the Best Historic Seaport Vacation Homes
Looking for the perfect place to stay in Historic Seaport? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Historic Seaport character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Historic Seaport Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Historic Seaport
- Pet Friendly
- Security/Safety
- Child Friendly
- Air Conditioner
- Pool
- TV
- Air Conditioner
- TV
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pool
Popular Neighborhoods for Historic Seaport Vacation Rentals
What are the best areas to stay in Historic Seaport
Discover the top neighborhoods in Historic Seaport and choose a place that suits your stay.
Sunday Jan 25
Historic Seaport, Key West
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Historic Seaport vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Historic Seaport
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- Pet Friendly
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How to Reserve Your Historic Seaport Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Historic Seaport Vacation Rental FAQs
1. What are the top vacation rentals in Historic Seaport?
There are a lot of options in Historic Seaport. If you plan on staying in the Historic Seaport area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Historic Seaport:
- *DARLING OF DUVAL @ OLD TOWN* Estate Cottage + Spa + LAST KEY SERVICES…
- *STAR OF THE SEAPORT @ OLD TOWN* Huge Home & Pool + LAST KEY SERVICES.
- "Tranquility " At Ann Street Gardens Steps From Duval
- *THE TOASTED COCONUT @ OLD TOWN* Fully Restored + Pool + LAST KEY SERVICES…
- *THE ZESTY LIME @ OLD TOWN* Beautifully Restored Home + LAST KEY SERVICES…
- NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
- Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- *THE LIME & THE COCONUT @ OLD TOWN* 6BR/6BA Compound + LAST KEY SERVICES.
- Ann Street Tranquility: A cozy and peaceful cottage
- Campbell Suite
2. How many vacation rentals have private pools in Historic Seaport?
There are 48 vacation rentals with private pools near Historic Seaport. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Historic Seaport are best for families?
If you are looking for a family-friendly vacation home in Historic Seaport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Historic Seaport:
4. How many vacation rentals are available in Historic Seaport?
Currently, the total number of properties listed in 2026 is over 632 in the Historic Seaport area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historic Seaport.