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 1 - 5 of 44 results matching your search criteria

Refine Search

Map View Grid view

List View

Add to Favorites

Admiral's Lane

Nightly and Weekly Rentals

4 Bedrooms

3 Bathrooms

Comfortably Sleeps 8

Max Occupancy 8

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old...

View Details

Add to Favorites

Truman House

Nightly and Weekly Rentals

4 Bedrooms

3 Bathrooms

Comfortably Sleeps 8

Max Occupancy 10

The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly...

View Details

Add to Favorites

Island Style

Nightly and Weekly Rentals

4 Bedrooms

3 Bathrooms

Comfortably Sleeps 8

Max Occupancy 8

If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies,...

View Details

Add to Favorites

Lady Emma

Nightly and Weekly Rentals

4 Bedrooms

2 Bathrooms

Comfortably Sleeps 8

Max Occupancy 8

There's something special about the kind of comfortable living afforded by this four bedroom, 2.5-bath, single-family home designated as "Lady Emma." The house takes its name from the street it inhabits, one of the most desirable addresses in town. It's part of Truman Annex, an award-winning...

View Details

Add to Favorites

The Mermaid's Garden

Nightly and Weekly Rentals

4 Bedrooms

3 Bathrooms

Comfortably Sleeps 8

Max Occupancy 8

Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical...

View Details