Key West vacation rentals
Vacation rentals in Key West by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Key West invites visitors with its historic landmarks like Ernest Hemingway's House, vibrant Duval Street, and sunset celebrations at Mallory Square. Travelers flock here for scuba diving in coral reefs, Hemingway Days, and the annual Fantasy Fest. Through Houfy, you can book directly with Key West hosts. Choose from charming Conch-style houses, downtown penthouses, and waterfront villas, situated near the Lower Keys and Dry Tortugas National Park. Visit between November and April for cooler temperatures and lively festivals.
Top-Rated Vacation Homes in Key West
Browse the highest rated vacation properties in Key West.
$9,722.25 USD total for 28 nights
Oct 25 – Nov 22, 2026
This is a great place to stay. The place is more beautiful than the pictures show. Just amazing. Great location. You can walk to anywhere in about 25 minutes (max) but there are several extremely good restaurants with in a 10-minute walk. The Catholic Church was a 10 minute walk and the neighborhood architecture is amazing. The place has two bicycles with it and you can ride anywhere on the island in 10 minutes. Very safe and friendly area, in fact the Old Town area was safe and friendly. The house is everything and more than you want and the pool is perfect. We were there the month of February and it was great. As far as Alan, anything you need he is there. Any questions he responded in less than an hour. Just a nice, relaxing place with a tone of nice people. Highly recommend the house and Key West. We will be back.
Why visit Key West
Discover what makes Key West a perfect vacation rental destination.
Pristine White Sands
Sunbathe or snorkel at Smathers Beach.
Smathers Beach, just 3 miles from downtown, offers powdery sands and vibrant marine life. Ideal for sunbathing and watersport enthusiasts.
Discover Historic Key West
Visit the Ernest Hemingway Home and Museum.
Only 0.5 miles from the city center, explore the Hemingway Home, where the renowned writer lived and penned classics.
Vibrant Nightlife Scene
Experience lively Duval Street venues.
Duval Street, located downtown, is famous for its vibrant bars and live music scene, perfect for night owls seeking local entertainment.
Explore Natural Beauty
Kayak through the mangroves at Fort Zachary Taylor.
Fort Zachary Taylor State Park, 1 mile away, offers scenic trails and kayaking opportunities in its lush mangrove ecosystems.
Where to stay in Key West
The best areas and neighborhoods for your vacation rental in Key West.
Old Town
Full of Victorian homes, unique shops, and historic landmarks, it's the cultural heart of Key West.
Bahama Village
Known for its Caribbean charm, vibrant street art, and eclectic stalls offering soul food and craft items.
New Town
A quieter area with shopping plazas, local markets, and residential streets, offering a more laid-back vibe.
Truman Annex
Gated area with luxurious accommodations and close proximity to beaches and the Truman Little White House.
Find Key West vacation rentals that suit your style
Condos, vacation homes and more — pick the kind of Key West vacation rental you want, then book it direct with the host.
Key West vacation rentals with free WiFi, hot tub or air conditioning
Free WiFi, hot tub, air conditioning and more — every Key West vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Key West
All within driving distance of Key West vacation rentals.
Ernest Hemingway Home and Museum
Renowned for its six-toed cats and deep literary heritage. · 0.5 miles
Duval Street
Iconic for its seafood joints and vibrant nightlife. · 0 miles
Fort Zachary Taylor State Park
Offers lush trails and pristine beaches. · 1 mile
Smathers Beach
A popular spot for sunbathing and windsurfing. · 3 miles
Harry S. Truman Little White House
President Truman's winter White House. · 1 mile
The Key West Butterfly & Nature Conservatory
Home to hundreds of exotic butterflies and birds. · 0.7 miles
Getting to and around Key West
Getting around Key West is easy with planes, bikes, and ferries available.
- KEY WEST INTERNATIONAL AIRPORT
- Located 3 miles from downtown, servicing flights from major cities.
- WE CYCLE
- Popular choice for getting around Key West efficiently and eco-friendly.
- KEY WEST FERRY TERMINAL
- Offers routes to nearby islands and mainland Florida.
Similar vacation rentals near Key West
Homes within 60 miles of Key West, from verified hosts.
$4,310.79 USD total for 7 nights
Feb 27 – Mar 6, 2027
$2,924.00 USD total for 7 nights
Oct 17 – 24, 2026
$2,140.00 USD total for 7 nights
Sep 20 – 27, 2026
Coastal Charm: Steps from the Beach, 2BR/2BA Condo, Pool View
$1,621.50 USD total for 7 nights
Sep 26 – Oct 3, 2026
$2,512.13 USD total for 7 nights
Sep 21 – 28, 2026
Bird of Paradise: Oceanfront Condo 3 BR, 2 BA with Heated Pool
$2,173.75 USD total for 7 nights
Sep 26 – Oct 3, 2026
Caribbean Sunsets: Open Gulf Views with Private Dock and Pool
$3,442.75 USD total for 7 nights
Sep 26 – Oct 3, 2026
Tropical Sunsets: Open Gulf Views with Private Dock and Pool
$4,145.40 USD total for 7 nights
Oct 3 – 10, 2026
$1,584.00 USD total for 7 nights
Sep 21 – 28, 2026
$2,467.13 USD $2,352.21 USD total for 7 nights
Sep 21 – 28, 2026
$2,203.00 USD total for 7 nights
Oct 17 – 24, 2026
Explore near Key West
Cities and towns within driving distance of Key West, each bookable direct with the host.
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More vacation rental destinations around Key West
Frequently asked questions
Quick answers about booking vacation rentals in Key West and what direct booking on Houfy actually means.
Rental prices range from $150 to over $500 per night, depending on location and amenities.
Yes, many rentals in Key West welcome pets. Verify pet policies with owners before booking.
Old Town and Bahama Village are popular for their historic charm and proximity to attractions.
For pleasant weather and events like Fantasy Fest, consider visiting between November and April.
Options include beachfront cottages, historic homes, and modern condos with various amenities.
Rentals offer more space and privacy, while hotels may provide extra services and central locations.
Check out the Key Lime Festival in the summer and relish local culinary traditions.
Houfy connects hosts and travelers directly. Book directly with owners.
Yes, Houfy is safe. Verify ratings and communicate with hosts directly for a secure experience.