Castle In Hawaii - Vacation Rentals in Historic Seaport

Ocean Key Resort & Spa, a Noble House Resort From US $579
         

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8.5 (101 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Ocean Key Resort - A Noble House Resort From US $760
         

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9.2 (1005 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Galleon Resort - Waterfront Key West
New
From US $731
         

New
Resort
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Luxury Places to Stay in Historic Seaport

Over 623+ Luxury Places to Stay in or Near Historic Seaport
Custom House Inn All From US $5,686
         

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New
Apartment
  • Security/Safety
  • Child Friendly
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 $4,660
         

NEW The Rigby House - Pvt Pool Amazing Location From US $4,615
         

New
House
  • Parking
  • Balcony/Terrace
  • Barbecue/Outdoor Cooking
Harbor Luxe Celebration Suites From US $4,304
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Commodore s Compound by Brightwild Huge Home From US $4,213
         

Top-Rated Vacation Rentals with a Pool in Historic Seaport

Over 438+ Top-Rated Vacation Rentals with a Pool in or Near Historic Seaport

Pet-Friendly Vacation Rentals in Historic Seaport

Over 202+ Pet-Friendly Vacation Rentals in or Near Historic Seaport
Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Commodore s Cove by Brightwild Epic Location From US $1,993
         

Rose Petal Petite Suite - Near Duval Street From US $593
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Classic Queen, Pet Friendly - Curry Mansion Inn From US $422
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Historic Seaport

Over 65+ Large Vacation Homes & Villas in or Near Historic Seaport
The Artist House From US $380
         

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9.5 (193 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor House Penthouse- A From US $2,543
         

9.8 (17 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Harbor Walk Hideaways | Group Compound In Old Town! From US $2,080
         

Wheelchair Accessible Vacation Homes in Historic Seaport

Over 206+ Wheelchair Accessible Vacation Homes in or Near Historic Seaport
Galleon Resort Efficiency in the old town From US $444
         

9.6 (157 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Key West Harbor Inn - Adults Only From US $320
         

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9.2 (293 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Pool
  • View
Amsterdam's Curry Mansion Inn From US $418
         

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8.4 (1005 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
Luxury Waterfront at Galion Resort in Old Town From US $816
         

Historic Seaport Varoom and Airbnb Places to Stay Under $200

Over 18+ Historic Seaport Varoom 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 378+ 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 Bartlum - Steps to Duval Street From US $640
         

9.6 (34 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
Kemp House From US $1,386
         

10.0 (6 Reviews)
House
  • Pool
  • TV
  • View

About Historic Seaport Vacation Rentals

With more than 40 Historic Seaport vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Castleinhawaii 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 Castleinhawaii 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 272.4 ft² on average, with prices averaging $1,690 a night.

Castleinhawaii 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
Resorts 35
Villas 4
Others 1

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

Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii 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