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Kemp House

Nightly and Weekly Rentals
3 Bedrooms
3.5 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...

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 getaway. This second-story, 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 steps from the...

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...

Coral Condo

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 4

Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island...

The Courtyard

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs,...

Shipyard

Nightly and Weekly Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give...

Writer's Retreat

Monthly and Seasonal Rentals
1 Bedroom
1.5 Bathrooms
Comfortably Sleeps 2
Max Occupancy 2

All you have to do is just show up. This cozy one-bedroom cottage has everything you need for your dream vacation. Inside the gated enclave, a large, heated, residents-only pool creates a visual centerpiece. It's easy to imagine yourself lazing in the shimmering turquoise water, on...

Calypso Cottage

Monthly and Seasonal Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

NEW UNIT!

When you're ready for a tropical vacation, Calypso Cottage is ready for you. This cozy one bedroom, one full bath Old Town property is one of the six stand-alone units that comprise the Land's End compound originally built for cigar workers back when the...

La Hacienda

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

FALL DISCOUNTS!

Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as you...

la Palm d'or

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

DECEMBER & JANUARY & MARCH Still Open!

The name of this home-Palm d'or-echoes the Palme d'Or, the highest award at the Cannes Film Festival. In this case, the award goes to the palm tree landscaping of this two-bedroom, two full-bath residence. The place is ringed in...

Amelia Lane

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

MARCH Still Open!

Sun, fun, and relaxation are the mainstays of life on the little island of Key West. To enjoy this tropical haven for yourself, the first step is securing the right accommodations. If a single-family home with three bedrooms, two full baths, a sparkling...

Blackbeard's Treasure

Monthly and Seasonal Rentals
3 Bedrooms
3.5 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

JANUARY Still Open!

In addition, save 3% off final negotiated rates if you pay by check.

To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era...

Ultimate Pool Cottage

Monthly and Seasonal Rentals
3 Bedrooms
3 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

SEASON 2019 Still Open!

This three-bedroom, three-full-bath cottage exudes the kind of at-ease ambiance that tells you you're right where you need to be to have the best vacation ever. The cottage is in the Meadows neighborhood on the grounds of an impressive Key West estate....

The Sanctuary

Monthly and Seasonal Rentals
5 Bedrooms
5 Bathrooms
Comfortably Sleeps 10
Max Occupancy 10

SEASON 2019 Still Open!

Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain...