You are here

Key West Vacation Rentals

Discover the Best Vacation Rentals in Key West

Our vacation home rentals in Key West are the perfect way to experience this special island. 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 a romantic getaway or a large group. 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 38 results matching your search criteria
Map ViewGrid view
List View

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...

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...

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...

Duval Square

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens...

Havana Hideaway

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing...

Pages