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 42 results matching your search criteria

Refine Search

Map View Grid view

List View

Add to Favorites

The Courtyard

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 2

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs,...

View Details

Add to Favorites

Rose Treehouse

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 2

Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the...

View Details

Add to Favorites

Ann Street Gardens

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 3

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come...

View Details

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

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