The Islands Advisors - Vacation Rentals in Historic Seaport

Amsterdam's Curry Mansion Inn From US $563
         

|
8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Artist House Key West From US $330
         

|
9.8 (431 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Designated Smoking Area
  • TV

Luxury Places to Stay in Historic Seaport

Over 628+ Luxury Places to Stay in or Near Historic Seaport
Bananas Foster by Brightwild Epic Guesthouse From US $5,606
         

New
House
  • Parking
  • Balcony/Terrace
  • Barbecue/Outdoor Cooking
1 Block to Duval St | Banana's Foster Guesthouse From US $4,855
         

9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Rigby House - Pool, One block from Duval St From US $4,184
         

Harbor Luxe Celebration Suites From US $3,894
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Commodore's Compound - One block from Duval St From US $3,861
         

9.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor Luxe Celebration Suites From US $3,808
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Top-Rated Vacation Rentals with a Pool in Historic Seaport

Over 445+ Top-Rated Vacation Rentals with a Pool in or Near Historic Seaport
Campbell Suite - In the heart of Old Town From US $413
         

Pet-Friendly Vacation Rentals in Historic Seaport

Over 196+ Pet-Friendly Vacation Rentals in or Near Historic Seaport
Harbor House Penthouse- A From US $1,817
         

10.0 (24 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Harbor House Penthouse- B From US $1,964
         

|
10.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
New The Cottage at James House From US $499
         

8.0 (2 Reviews)
Apartment
  • Pet Friendly
  • Pool
  • Balcony/Terrace
The Curry Poolside | Ground Floor King From US $503
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Historic Seaport

Over 64+ Large Vacation Homes & Villas in or Near Historic Seaport
The Artist House From US $387
         

|
9.5 (193 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Custom House Inn | 8 BR Suite Compound on Duval! From US $3,546
         

10.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Security/Safety
Commodore's Cove - One block from Duval St From US $1,583
         

8.8 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Historic Seaport

Over 208+ Wheelchair Accessible Vacation Homes in or Near Historic Seaport
Key West Harbor Inn - Adults Only From US $320
         

|
9.2 (273 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pool
  • View
Amsterdam's Curry Mansion Inn From US $265
         

|
8.2 (1005 Reviews)
House
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Galleon Resort Efficiency in the old town From US $321
         

9.6 (160 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury Waterfront at Galion Resort in Old Town From US $848
         

Sunset views at the Galleon From US $899
         

9.6 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Historic Seaport Vacation Rentals and Airbnb Places to Stay Under $200

Over 17+ Historic Seaport Vacation Rentals and Airbnb Places to Stay Under $200
ISLAND PEARL - Cozy Nightly Rental just off Duval RealKeyWest From US $149
         

Instantly Bookable Vacation Homes in Historic Seaport

Over 374+ Instantly Bookable Vacation Homes in or Near Historic Seaport
Pool, Pet Friendly, & Near Duval - Sugar Pie Suite From US $459
         

9.4 (9 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
The Penthouse at Custom House Inn | New! From US $1,175
         

10.0 (23 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Courtyard - Condo in Downtown Key West! From US $422
         

The Gideon Lowe House - Old Town Key West From US $787
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Historic Seaport Vacation Rentals

With more than 637 Historic Seaport vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Theislandsadvisors and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Historic Seaport.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Theislandsadvisors Historic Seaport, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Historic Seaport. Places to stay near Historic Seaport are 636.49 ft² on average, with prices averaging $1,132 a night.

Theislandsadvisors makes it easy and safe to find and compare vacation rentals in Historic Seaport with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Historic Seaport

Type Count
Vacation Homes 241
Holiday Apartments 140
Hotels with Suites 112
Resorts 37
Cottages 12
B&B 9
Villas 4
Others 1

Use these Quick Filters to Find a Vacation Rental in Historic Seaport

Pro Tip: Theislandsadvisors makes it easy to compare the best listings on Theislandsadvisors homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Theislandsadvisors homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Historic Seaport.

Weather in Historic Seaport

View the weather forecast for Historic Seaport before booking your Historic Seaport Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Historic Seaport Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Historic Seaport?
How many vacation rentals are available in Historic Seaport?

Currently, the total number of properties listed in 2026 is over 637 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.