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.

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Displaying 6 - 10 of 39 results matching your search criteria

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Valhalla

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...

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Havana Hideaway

Nightly and Weekly Rentals

2 Bedrooms

2 Full - 1 Half Bathrooms

Comfortably Sleeps 4

Max Occupancy 5

DISCOUNTED Monthly stays this summer! See Rate Tab!

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...

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Royal Palm

Nightly and Weekly Rentals

2 Bedrooms

2 Full - 1 Half 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...

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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...

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La Prive

Nightly and Weekly Rentals

2 Bedrooms

2 Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

(For 2021 arrival date bookings only monthly stays are being accepted. 2022 is available for short- and long-term stays, please see minimum night stay information on rate tab.)

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full...

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