Rent Luxury Holiday Cottages in Key West

We selected the 18 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

Orange & Sand

Orange & Sand

  • 6 guests

  • 3 bedrooms

Harbor Beach, Fort Lauderdale

A private dock on the canals of Fort Lauderdale and your own swimming pool by the waterside – this cosy cottage is ideal for boaties and waterbabies. If you’re not exploring the area by kayak, boat or paddleboard, you can rent bikes and go by land.

Wake Up With the Sun

Wake Up With the Sun

  • 6 guests

  • 3 bedrooms

Atlantis, Florida

Spend just a few moments admiring the views of the small lake and verdant fairways, and you'll understand why this contemporary bungalow is a relaxing retreat. Situated in the gated Atlantis community, this home oozes sparkle.

Dream In Coral

Dream In Coral

  • 6 guests

  • 3 bedrooms

Coral Way, Miami

With its tasteful yet laid back aesthetic, this charming three bedroom home to the south of Downtown Miami is a wonderful find. Nestled in Coral Way, you'll find a classily furnished living room leading into an equally sophisticated dining area.

Coconut Bay

Coconut Bay

  • 10 guests

  • 4 bedrooms

Southwest Coconut Grove, Miami

Nestled in Miami's oldest neighbourhood, Coconut Grove, this charming Florida cottage is all lush greenery, sunshine and classic character. Inside, it’s bright and inviting, with a kitchen for relaxed cooking and a separate dining room for memorable meals.


We selected the top 3% holiday homes in Key West Cottages

Explore the 18 most perfect homes in our collection

View on map

Most popular homes in Key West

Miami Modern

Miami Modern

  • 8 guests

  • 3 bedrooms

Coral Way, Miami

Love Is A Dream

Love Is A Dream

  • 12 guests

  • 3 bedrooms

Richmond West, Miami-Dade County

Queen of the River

Queen of the River

  • 2 guests

  • 1 bedrooms

Little Haiti, Miami

Sunshine Sleeper

Sunshine Sleeper

  • 6 guests

  • 2 bedrooms

Cutler Bay, Miami-Dade County

Key to the Garden

Key to the Garden

  • 10 guests

  • 4 bedrooms

Miami-Dade County, Florida

View all

Check upcoming rates & availability for Key West Cottages


Frequently asked questions

Similar destinations

Discover our curated collection of luxury holiday Cottages in Key West, Monroe County, Florida, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Key West Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

Search our collection