Key West Vacation Rentals

Browse the best rentals in Key West

Vacation rentals in Key West are perfect places to experience this special island. Every Key West rental has its own distinct charm. As one of Key West’s first property management companies, we represent some of the best rentals in Key West’s diverse communities. Many of our historic homes, villas, and condos come complete with private pools and beautiful outdoor areas that are great for singles, couples and families alike. We work closely with our guests to ensure that you receive personal service throughout your Key West Vacation.

Book a Dream Vacation to Key West today!

Displaying 21 - 25 of 39 results matching your search criteria

Refine Search

Map View Grid view

List View

Add to Favorites

Bella Vita

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 2

Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That's why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a...

View Details

Add to Favorites

Conch in Training

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 4

The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living...

View Details

Add to Favorites

Coral Condo

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 4

Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island...

View Details

Add to Favorites

Poinciana House

Nightly and Weekly Rentals

1 Bedroom

2 Bathrooms

Comfortably Sleeps 2

Max Occupancy 4

Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging back...

View Details

Add to Favorites

The Sanctuary

Monthly and Seasonal Rentals

5 Bedrooms

5 Bathrooms

Comfortably Sleeps 10

Max Occupancy 10

Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower. Five doors of...

View Details