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Key West vacation rentals

Vacation rentals in Key West by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.

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.

$9,646.75 USD total for 28 nights

Apr 1 – 29, 2027

Great accommodation and location!!
Just finished up a month (4/4/25-5/5/25) long stay at this location. It was a perfect location just a 1/2 block off Duval. The home is larger than the photos would appear. The front room is converted to a bedroom, so it's really 3 bedrooms. Very clean and well maintained. Great entertaining area outside with small soaking pool, a hot tub and a spacious outdoor area. I come down to Key West 3-4 times a year for the past 14 years. (so i've stayed in quite a few places). This location left me pleasantly surprised. The host were also very accommodating (we had airline issues/cancellation) and help us out with an extra day with only an hours notice. Will definitely look at this place in the future...
D. · Stay April 2025

FREE TIME Vibes

2 bd·2 ba
5· 5

$3,706.00 USD total for 3 nights

Nov 5 – 8, 2026

This boat has great space and amenities. I shared this trip with my teenage daughter along with my brother and his two teenaged kids. We loved the outside spaces as well as inside salon to enjoy family time. Peaceful mornings on the top deck during sunrise listening to the tarpon hunting in the marina. The marina is quiet and welcoming. We enjoyed using the pool along with the hammocks looking out to the Atlantic. Everyone also had enough space if they needed alone time (teenagers 😂). Kitchen is great and we were able to cook breakfast before our daily adventures on Key West and then dinner each day when we returned. We also took advantage of their smaller boat for 2 excursions, snorkeling and sandbar. Cor has a great “man on the ground,” JB who set the excursions up and checked in frequently to make sure our stay was great. If you have ever wanted to stay on a boat but worry about being on water, staying here is a great option. This place is definitely on my “return to list.”
B. · Stay August 2026

Recommended Homes in Key West

Handpicked properties we think you'll love in Key West.

Shipwreck Suite

1 bd·1 ba

$5,937.28 USD total for 28 nights

Dec 6, 2026 – Jan 3, 2027

Casa Mamisa

2 bd·2 ba

$16,191.50 USD total for 28 nights

Mar 1 – 29, 2027

William Skelton Home

6 bd·4 ba

$4,006.75 USD total for 3 nights

Dec 6 – 9, 2026

Reynolds Paradise

2 bd·2 ba

$5,369.57 USD total for 28 nights

May 31 – Jun 28, 2027

Old Town Key West Cottage

2 bd·1½ ba

$8,080.01 USD total for 28 nights

Apr 15 – May 13, 2027

William Skelton Home - Upstairs

3 bd·2 ba

$3,087.90 USD total for 3 nights

Dec 6 – 9, 2026

Duval & Catherine St

2 bd·1 ba

$10,052.00 USD total for 28 nights

Apr 2 – 30, 2027

Pet friendly vacation rentals in Key West

Bring your furry friend along! Browse pet-welcoming homes in Key West.

$972.00 USD total for 3 nights

Nov 9 – 12, 2026

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.

Best for: history lovers, architecture enthusiasts, families

Bahama Village

Known for its Caribbean charm, vibrant street art, and eclectic stalls offering soul food and craft items.

Best for: foodies, art seekers, cultural enthusiasts

New Town

A quieter area with shopping plazas, local markets, and residential streets, offering a more laid-back vibe.

Best for: families, long-term stays, quieter vacations

Truman Annex

Gated area with luxurious accommodations and close proximity to beaches and the Truman Little White House.

Best for: luxury travelers, beachgoers, history buffs

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

Best Time to Visit Key West

Key West offers warm temperatures year-round, 70-90°F. Best months for a visit are March to May with clear skies and mild humidity.

The best time to visit Key West is December to April, when the weather is at its best.

Best weatherDec – Apr
Best valueSep

OctNow

85°F29°C

Rainfall Moderate

Demand Mid

Nov

81°F27°C

Rainfall Moderate

Demand Mid

Dec

77°F25°C

Rainfall Low

Demand Mid

Jan

75°F24°C

Rainfall Low

Demand Mid

Feb

76°F24°C

Rainfall Low

Demand Mid

Mar

78°F26°C

Rainfall Low

Demand Peak

Apr

81°F27°C

Rainfall Low

Demand Peak

May

84°F29°C

Rainfall Moderate

Demand Peak

Jun

87°F31°C

Rainfall High

Demand Mid

Jul

89°F32°C

Rainfall High

Demand Mid

Aug

89°F32°C

Rainfall High

Demand Mid

Sep

88°F31°C

Rainfall High

Demand Low

Getting to and around Key West

Getting around Key West is easy with planes, bikes, and ferries available.

Airport
KEY WEST INTERNATIONAL AIRPORT
Located 3 miles from downtown, servicing flights from major cities.
Bike Rentals
WE CYCLE
Popular choice for getting around Key West efficiently and eco-friendly.
Ferry
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.

Stay Anchored at Sombrero

4 bd·3 ba
5· 19

$4,432.46 USD total for 7 nights

Feb 27 – Mar 6, 2027

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

3 bd·2 ba
4.94· 16

$2,924.00 USD total for 7 nights

Nov 14 – 21, 2026

$1,640.00 USD total for 7 nights

Nov 7 – 14, 2026

$1,621.50 USD total for 7 nights

Nov 14 – 21, 2026

Tropical Keys sanctuary steps from private beach.

2 bd·2 ba
4.89· 142

$2,140.00 USD total for 7 nights

Nov 5 – 12, 2026

$3,813.75 USD total for 7 nights

Nov 5 – 12, 2026

$3,865.75 USD total for 7 nights

Nov 14 – 21, 2026

$2,173.75 USD total for 7 nights

Nov 7 – 14, 2026

$3,442.75 USD total for 7 nights

Nov 14 – 21, 2026

Waterfront Home - Incredible View, 37' Dock, Kayak

2 bd·2 ba
4.77· 13

$1,584.00 USD total for 7 nights

Nov 5 – 12, 2026

Keys Waterfront- Spectacular Gulf View, Dock, Pool

3 bd·1 ba
4.5· 10

$2,602.13 USD $2,480.46 USD total for 7 nights

Nov 5 – 12, 2026

Explore near Key West

Cities and towns within driving distance of Key West, each bookable direct with the host.

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Quick answers about booking vacation rentals in Key West and what direct booking on Houfy actually means.

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