Book a stay in one of the best homes in Key West

We selected the 318 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Key West

The Pearl of Key West

The Pearl of Key West

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

Spend your days soaking up the island breeze at this laid-back retreat just outside Key West. Tucked inside a quiet gated community, this spacious six-bedroom home is made for group getaways, with a private boat slip, breezy balconies, and enough room for everyone to spread out.

Island Sophisticate

Island Sophisticate

  • 16 guests

  • 6 bedrooms

Key Haven, Key West

This impeccably decorated home is a masterclass in island elegance, where every detail has been thoughtfully designed for comfort and style. It's light-filled, spacious, and beautifully finished with a refined, coastal touch.

Salt and Serenity

Salt and Serenity

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Tucked along the water’s edge just minutes from Key West, this breezy four-bedroom retreat blends comfort with coastal charm. With a private heated pool, gated garden, and dock for boats up to 50 feet, it’s made for both downtime and days on the water.

Key Sunset

Key Sunset

  • 14 guests

  • 5 bedrooms

Key Haven, Key West

If you’ve ever dreamed of a tropical getaway in the sun, with palm trees swaying and crystal blue waters visible from the kitchen window, this is the place for you. Located in the iconic Key West, this five-bedroom home offers every comfort you’d expect from a Floridian home right on the water – including a fenced pool, a spacious and fully-equipped kitchen, and even your own private dock extending into the sea.


We selected the top 3% holiday homes in Key West

Explore the 318 most perfect homes in our collection

View on map

Most popular homes in Key West

Dockside Dreams

Dockside Dreams

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

 Shellstone Magic

Shellstone Magic

  • 16 guests

  • 8 bedrooms

Key Haven, Key West

Key West Retreat

Key West Retreat

  • 12 guests

  • 4 bedrooms

Key Haven, Key West

 Marina Living

Marina Living

  • 18 guests

  • 8 bedrooms

Key Haven, Key West

The New Standard

The New Standard

  • 20 guests

  • 8 bedrooms

Key Haven, Key West

Sunset Key

Sunset Key

  • 10 guests

  • 4 bedrooms

Key Haven, Key West

Key Lime Delight

Key Lime Delight

  • 16 guests

  • 5 bedrooms

Key Haven, Key West

Keys to Paradise

Keys to Paradise

  • 14 guests

  • 6 bedrooms

Key Haven, Key West

View all

Check upcoming rates & availability for Key West


Frequently asked questions