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 11 - 15 of 45 results matching your search criteria

Refine Search

Map View Grid view

List View

Add to Favorites

Royal Palm

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 5

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and...

View Details

Add to Favorites

Duval Square

Nightly and Weekly Rentals

2 Bedrooms

2 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...

View Details

Add to Favorites

Banana Key

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 5

Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...

View Details

Add to Favorites

La Prive

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound...

View Details

Add to Favorites

Duval Street Suite

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 6

It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment.

From your private and...

View Details