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 16 - 20 of 44 results matching your search criteria

Refine Search

Map View Grid view

List View

Add to Favorites

Shipyard

Nightly and Weekly Rentals

2 Bedrooms

1 Bathroom

Comfortably Sleeps 4

Max Occupancy 4

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give...

View Details

Add to Favorites

Conch in Training

Nightly and Weekly Rentals

1 Bedroom

1 Bathroom

Comfortably Sleeps 2

Max Occupancy 4

This home is, or may soon be, listed for sale. Guests booking this home must agree to showing requests. We ask the listing agents/companies to limit showings to two times per week, with 24-hour notice, but cannot guarantee compliance with the number of showings. For details...

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

Campbell Suite

Nightly and Weekly Rentals

1 Bedroom

1 Full - 1 Half Bathrooms

Comfortably Sleeps 2

Max Occupancy 2

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect place to anchor your vacation. It starts with the white...

View Details