Old Town Vacation Homes

Key West Old Town Vacation Home living room and kitchen

Your Island Getaway in Key West

Our Key West vacation rentals offer the ultimate waterfront experience, with 29 luxurious properties available for your perfect island escape. Whether you’re staying in a historic home, condo, or a property with a private boat slip, you’ll enjoy stunning ocean views, accommodations for up to 10 guests, and all the amenities you need for a comfortable stay. Many of our properties reflect the classic conch architecture that Key West is known for, blending island charm with modern conveniences like high-speed wireless internet, spacious living areas, and multiple TVs. Dog-friendly options are also available, so everyone in your family can enjoy paradise together.

LIMITED TIME OFFER

Save 15%* On Your First Stay

For a limited time, save 15%* on your first stay and enjoy all the comforts of home in a city full of history!

Use promo code HTA15 or call 305-292-8905.

*Limited time offer. Excludes holidays or special event dates. Based on availability. Not available with other discounts. Valid for first-time stay only. Use promo code HTA15 when you fill out form or by calling 305-292-8905. Other restrictions may apply.

Expert Hospitality and Local Insights

Our team brings years of experience in the hospitality industry, ensuring that your Key West vacation is as enjoyable as it is seamless. As locals of Key West, we provide personalized recommendations and insider tips to help you explore the island like a true local. Our white-glove concierge service is available to meet all your needs, whether you’d like a gourmet meal delivered to your rental, assistance with laundry, or suggestions for the best-hidden spots in town. We are here to make your stay effortless, comfortable, and unforgettable.

Key West Old Town Vacation Home bedroom

We are here to make your stay effortless, comfortable, and unforgettable...

Key West Old Town Vacation Home living room and bedroom

Explore the Best of Key West’s History

Our waterfront rentals are ideally located to help you experience everything that makes Key West special. Situated near historic sites like the Ernest Hemingway Home and the Southernmost Point, our properties place you in the heart of this island’s storied past. You can explore the island’s rich maritime history, visit Fort Zachary Taylor, or take a day trip to Dry Tortugas National Park. After a day of adventure, return to your luxurious home and relax on a private balcony, watching the sunset over the ocean. Whether you’re here for history, outdoor adventures, or simply to unwind, our Key West rentals offer the perfect home for your stay.

Key West Old Town Vacation Home standing on balcony looking at the water