Discover Your Perfect Key West Harbour Vacation Homes

Best Vacation Homes in Key West Harbour

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House
Mastway House -Pool & Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Key West Harbour Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Key West Harbour Vacation Rentals

Where are the best neighborhoods to stay in Key West Harbour?

When considering where to stay in Key West, the Harbour neighborhood offers a peaceful yet conveniently located option for your vacation. This area provides easy access to the scenic waterfront and a relaxed atmosphere that embodies the island’s charm. Choosing accommodations in Key West Harbour allows you to enjoy a serene environment while remaining close to key attractions and amenities. It’s an ideal setting for those seeking comfort and tranquility during their getaway on this beautiful Florida island.

Key West Historic District

Staying in this area places you at the heart of Key West's rich history, offering a charming atmosphere filled with historic architecture and cultural landmarks. It's an ideal choice for those seeking an authentic experience close to the region’s iconic sites.

View 2939+ Rentals in Key West Historic District

Old Town

Choosing accommodation here immerses you in the lively and vibrant core of Key West, perfect for exploring local shops, restaurants, and art galleries. The neighborhood provides a convenient base to enjoy the area's unique Caribbean charm.

View 2856+ Rentals in Old Town

Sunset Key

This secluded island destination offers tranquil surroundings and luxurious retreats just a short ferry ride from the mainland, making it a peaceful escape within the region’s scenic views.

View 3214+ Rentals in Sunset Key

Downtown

Staying downtown puts you in close proximity to bustling nightlife, lively entertainment, and waterfront activities, perfect for those looking to experience the energetic vibe of the area.

View 1275+ Rentals in Downtown

Uptown - Upper Duval

In this part of the city, you'll find a mix of historic neighborhoods and modern amenities, ideal for visitors wanting to explore both the cultural heritage and contemporary offerings of the region.

View 890+ Rentals in Uptown - Upper Duval

Bahama Village

Known for its colorful Caribbean influences, this vibrant neighborhood offers a lively community atmosphere, great for discovering local cuisine and arts within the area.

View 107+ Rentals in Bahama Village

New Town

Opting for accommodations here grants easy access to key transportation routes and a quieter setting while still being close enough to enjoy all the attractions the region has to offer.

View 125+ Rentals in New Town

Historic Seaport

This waterfront locale is perfect for those interested in maritime history, offering picturesque views and proximity to boat tours and waterfront dining experiences.

View 462+ Rentals in Historic Seaport

Best Times to Visit Key West Harbour

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination ensures you enjoy its vibrant atmosphere and pleasant weather, making your stay in Key West Harbour truly memorable.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak tourist season as travelers escape colder climates for the warm, sunny weather. Expect lively atmospheres and a bustling waterfront scene.

Average Temperature Daytime: around 75°F - Nighttime: about 65°F
spring
Spring (March to May)

Spring draws visitors seeking pleasant temperatures and vibrant local events. The area buzzes with activity, making it an ideal time to explore the local waterside attractions.

Average Temperature Daytime: mid-70s to low 80s°F - Nighttime: mid-60s°F

Off-Season Highlights

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Summer (June to August)

The summer months see a slight dip in visitor numbers, offering a quieter experience while still enjoying warm weather and excellent conditions for watersports.

Average Temperature Daytime: high 80s to low 90s°F - Nighttime: mid to high 70s°F
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Fall (September to November)

Fall tends to be less crowded, providing a more relaxed atmosphere for exploring the area's scenic views and local culture. The weather remains warm, perfect for outdoor activities.

Average Temperature Daytime: mid-80s°F - Nighttime: mid-70s°F

Weekly Weather Forecast for Key West Harbour

How to Book Your Key West Harbour Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Key West Harbour

More Top-Rated Vacation Rentals in Key West Harbour Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to a private, scenic outdoor swimming pool perfect for relaxing in the sunshine.
  • Take advantage of well-maintained outdoor grilling areas to prepare meals while enjoying the coastal breeze.
  • Relax on spacious outdoor patios or decks that offer stunning views of the surrounding waterways.
  • Make use of lush landscaped gardens and tropical landscaping that add to the region’s seaside charm.
  • Participate in water-based activities like kayaking or paddleboarding available nearby for outdoor enthusiasts.
  • Benefit from secure, off-street parking in the outdoor designated parking spaces within the community.
  • Stroll through beautifully maintained pathways that wind around the property, ideal for leisurely walks near the water.

Top Attractions Around Key West Harbour

What attractions are nearby?

During your stay, you'll find a variety of exciting activities nearby that showcase the vibrant culture and natural beauty of this destination, making it an ideal choice for exploring the region's unique charm and outdoor recreation options.

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Family Activities

  • Eco-Discoveries at the Key West Harbour Marine Sanctuary: Explore the region's vibrant marine life through guided eco-tours, perfect for engaging family members of all ages with the area's natural beauty.
  • Captain’s Pirate Ship Adventure: Set sail on a family-friendly pirate cruise that entertains children with interactive storytelling while offering stunning views of the surrounding waters.
  • Kayaking and Paddleboarding in the Harbor: Rent kayaks or paddleboards to enjoy the calm waters directly from this destination, providing a fun and active way for families to explore the scenic harbor area.
  • Fishing Excursions in Key West Bay: Join a fishing tour tailored for families, offering an exciting opportunity to learn about the region’s aquatic ecosystem while trying your luck at catching local fish species.
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Adult Activities

  • Sunset Sailing Tours: Embark on a relaxing cruise to witness stunning sunsets over the harbor, offering unforgettable views in this scenic destination.
  • Fishing Excursions: Try your hand at deep-sea or bay fishing, where expert guides will take you out to the best spots in this maritime region.
  • Stand-Up Paddleboarding: Explore the calm waters of the harbor with stand-up paddleboarding, enjoying both exercise and scenic vistas in this popular area.
  • Kayaking Adventures: Discover hidden coves and local wildlife by paddle kayak, immersing yourself in the natural beauty that surrounds here.

Key West Harbour Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Water Activities: Take advantage of the region's vibrant culinary scene and water-based adventures to fully immerse yourself in the local vibe.
  • Plan Your Outings Around Sunset Views: Schedule boat trips or outdoor activities during sunset hours to experience the area's renowned evening beauty.
  • Choose a Prime Waterfront Property: Select accommodations with direct water access or scenic views to enhance your experience of this coastal destination.
  • Utilize Local Transportation Options: Make use of bikes, ferries, or taxis to conveniently navigate between popular spots around here’s lively harbor and beyond.

Transportation Options

  • Ferry Services: You can effortlessly explore the region with ferry options that connect Key West Harbour to nearby islands and attractions, offering scenic views and a relaxing ride.
  • Charter Boats: Private or group charter boat services provide an exclusive way to enjoy the waters, whether for sightseeing, fishing, or sunset cruises around this coastal destination.
  • Public Transit: Local bus and shuttle services ensure convenient transportation within the area, making it easy for you to access key points of interest from your rental.
  • Rental Cars and Bicycles: For flexible exploration at your own pace, on-site car rentals and bike-sharing programs offer ideal ways to discover this vibrant regional hub.

Local Customs Options

  • Gulf Coast Greetings: Locals in this area often greet visitors with a friendly "Hello" accompanied by a nod, reflecting the region's welcoming maritime culture.
  • Respect for Marine Etiquette: It’s customary here to show respect for the ocean and its surroundings, especially during boat outings or while enjoying waterfront dining.
  • Festive Celebrations: Participating in local festivals and events is common, where lively music, colorful parades, and traditional foods showcase regional pride.
  • Casual Dress Code: Visitors are encouraged to dress comfortably and casually, embracing the relaxed island lifestyle that defines this destination.

Frequently Asked Questions About Key West Harbour?

1. What are the top vacation rentals in Key West Harbour?

There are a lot of options in Key West Harbour. If you plan on staying in the Key West Harbour area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Key West Harbour:

2. How many Rentbyowner vacation rentals are available in Key West Harbour?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1159 in the Key West Harbour area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Key West Harbour. 

3. What is the cancellation policy for booking a vacation rental here?

The cancellation policy varies depending on the specific property you choose. To understand the details, please review the listing’s cancellation terms or contact the property owner directly before confirming your reservation.

4. Are there any additional fees I should be aware of when booking?

Additional fees such as cleaning fees, service charges, or taxes may apply and will be detailed in the listing. It’s advisable to review all fee information carefully on the property page or reach out to the owner for clarification.

5. What amenities are included with my stay in this destination?

Amenities differ between properties, so it’s best to check the listing description for specifics like Wi-Fi, parking, or kitchen facilities. For further inquiries, contacting the owner can help ensure the property meets your needs.

6. How do I inquire about availability or special requests?

Availability can be checked directly through the booking platform by selecting your preferred dates. For special requests or questions about the property, reaching out to the owner is recommended to confirm details before booking.

7. Is there a minimum stay requirement for booking?

Minimum stay requirements depend on the individual property. Details regarding length of stay are typically listed on the property page, or you can contact the owner to clarify the booking policies.

Best Vacation Homes in Key West Harbour