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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 39 results matching your search criteria
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Admiral's Lane

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

DISCOUNTED Monthly stays this summer! See Rate Tab!

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

As part...

Truman House

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 10

(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.)

The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's...

The Mermaid's Garden

Nightly and Weekly Rentals
4 Bedrooms
3 Full - 2 Half Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

DISCOUNTED Monthly stays this summer! See Rate Tab!

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

Noah's Retreat

Nightly and Weekly Rentals
3 Bedrooms
3 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

NEW UNIT! START UP SPECIALS!

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...

Kemp House

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

(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 Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block...

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