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 39 results matching your search criteria

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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...

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Quilted Giraffe

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.)

Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you...

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The Meadows House

Nightly and Weekly Rentals

2 Bedrooms

2 Full - 1 Half Bathrooms

Comfortably Sleeps 4

Max Occupancy 4

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...

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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...

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Shipyard

Nightly and Weekly Rentals

2 Bedrooms

1 Bathroom

Comfortably Sleeps 4

Max Occupancy 4

(For new 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 cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The...

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