Key West Vacation Rentals
Browse Key West vacation rentals with Seven Keys Vacations and find a stay that puts you close to the color, character, and energy of the island. Our Key West rentals include historic homes, Conch-style cottages, coastal condos, private pool homes, and comfortable vacation homes for couples, families, groups, and longer island stays.
Key West is one of the most unique destinations in the Florida Keys. Days can start with coffee on a shaded porch, continue with a bike ride through Old Town, a beach stop, a fishing charter, or time along the Historic Seaport, and end with dinner, live music, and a sunset near Mallory Square. Unlike many island destinations, Key West is easy to explore without packing every outing into the car.
Find the Right Key West Rental for Your Trip
Many guests choose Key West vacation homes for their privacy, outdoor space, and sense of place. Look for classic island details like tropical courtyards, porches, private pools, lush landscaping, and walkable locations near dining, shopping, beaches, marinas, and local attractions. If a pool is high on your list, browse our Florida Keys rentals with private pools. You can also explore pet-friendly rentals or homes with an ocean view.
Key West offers several different ways to stay. Old Town is ideal for guests who want historic charm, walkability, and easy access to Duval Street, Mallory Square, and the waterfront. Quieter residential pockets work well for travelers who want a calmer retreat after a busy day. Condo rentals can be a convenient option for smaller groups, while larger Key West house rentals are a strong fit for families and friends traveling together.
If you are comparing areas across the island chain, you may also want to browse Lower Keys vacation rentals for a quieter stay near Key West, or view our full collection of Florida Keys vacation rentals. Planning a longer visit? Explore weekly rentals in the Florida Keys or monthly rentals in the Florida Keys for more time to settle into island life.
Browse available Key West vacation rentals below and book direct with Seven Keys Vacations for a more personal, locally focused rental experience.
Tell us what you're looking for and someone will contact you with available options.
Key West Vacation Rental FAQs
What is the best area to stay in Key West?
The best area to stay in Key West depends on the type of trip you are planning. Old Town is a popular choice for guests who want walkability, historic charm, restaurants, shops, nightlife, and easy access to Duval Street and the waterfront. Quieter residential areas can be a better fit for travelers who want a more relaxed home base with private outdoor space, while still being close to the island’s main attractions.
Are Key West vacation rentals walkable?
Many Key West vacation rentals are close to restaurants, shops, beaches, marinas, and attractions, especially rentals in or near Old Town. Key West is also popular for biking and golf carts, so guests often choose a rental based on how close they want to be to Duval Street, Mallory Square, the Historic Seaport, beaches, or quieter neighborhood streets.
Do Key West vacation rentals have private pools?
Some Key West vacation rentals include private pools, plunge pools, tropical courtyards, or shaded outdoor living areas. These features are especially popular for guests who want a private place to relax between beach days, sightseeing, boating, and evenings out. You can browse Florida Keys rentals with private pools to compare available homes with pool access.
Is Key West a good place to stay without a car?
Key West can be a great destination without a car, especially for guests staying near Old Town, Duval Street, the Historic Seaport, or other central areas. Many visitors walk, bike, use rideshare, rent golf carts, or take local transportation once they arrive. If you plan to explore beyond Key West, a car may be helpful for day trips into the Lower Keys or other parts of the Florida Keys.
Are there weekly or monthly rentals in Key West?
Yes, some Key West vacation rentals are available for longer stays, including weekly and monthly visits. Longer stays are a good fit for snowbirds, remote workers, seasonal guests, retirees, and travelers who want more time to settle into the island routine. Browse weekly rentals in the Florida Keys or monthly rentals in the Florida Keys to compare extended stay options.
Are there pet-friendly vacation rentals in Key West?
Pet-friendly options may be available depending on the property, dates, and rental requirements. Guests traveling with dogs should review each listing carefully for pet policies, fees, size limits, outdoor space, and neighborhood fit. You can start by browsing our pet-friendly rentals in the Florida Keys.
Should I stay in Key West or the Lower Keys?
Choose Key West if you want walkability, nightlife, restaurants, historic streets, shopping, sunset celebrations, and a lively island setting. Choose the Lower Keys if you want a quieter stay with more nature, boating, wildlife, and easy day-trip access to Key West. Guests who want both often compare Key West vacation rentals with Lower Keys vacation rentals before booking.
