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 37 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

Early Bird Summer/Fall Specials! This unit is available for monthly rental only, during select summer into fall months at a BIG Savings. Please see the rate tab under the unit page for details, or call our office!!

The Keys have some of the most charming, top-rated...

View Details

Add to Favorites

Kemp House

Nightly and Weekly Rentals

3 Bedrooms

3 Full - 1 Half Bathrooms

Comfortably Sleeps 6

Max Occupancy 6

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only...

View Details

Add to Favorites

Noah's Retreat

Nightly and Weekly Rentals

3 Bedrooms

3 Bathrooms

Comfortably Sleeps 6

Max Occupancy 6

If you are in a Key West state of mind, you are going to find "Noah's Retreat," a custom-built home, ideal for your vacation rental: 3 bedrooms, 3 baths, dedicated parking, and professional landscaping around a climate-controlled private pool. All this in the most desirable gated...

View Details