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Admiral's Lane

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

PRE-SUMMER Special pricing until JULY!

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House...

Hermitage South

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

PRE-SUMMER Special pricing until JULY!

The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist...

Kemp House

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

PRE-SUMMER Special pricing until JULY!

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...

La Prive

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

PRE-SUMMER Special pricing until JULY!

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...

Conch in Training

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

PRE-SUMMER Special pricing until JULY!

The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place...

Hilltop Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

PRE-SUMMER Special pricing until JULY!

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath...

Azure Hideaway

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

PRE-SUMMER Special pricing until JULY!

So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure...

La Hacienda

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

PRE-SUMMER Special pricing until JULY!

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...

En Plein Air

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

PRE-SUMMER Special pricing until JULY!

En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling...

Blackbeard's Treasure

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

NEW / LOWER OFF SEASON RATES!

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....

Amelia Lane

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

PRE-SUMMER Special pricing until JULY!

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,...

Amelia by the Sea

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

NEW UNIT!

This superbly designed three-bedroom, two-bath conch house named "Amelia By the Sea" is located, as the name suggests, near sandy beaches and the wildly beautiful Atlantic Ocean. It's part of Bahama Village, a 16-block historic subsection of Old Town Key West that hosts some...

Paradise Grand

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

PRE-SUMMER Special pricing until JULY!

Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small...