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The Mermaid's Garden

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

SPECIAL WINTER PRICING - NOW Through the end of JANUARY!

Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized...

Island Style

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

SPECIAL WINTER PRICING - NOW Through the end of FEBRUARY for OPEN DATES!

If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has...

Admiral's Lane

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

SPECIAL FEBRUARY DISCOUNT for OPEN DATES! See Rate Table.

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...

Lady Emma

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

SPECIAL WINTER PRICING - NOW Through the end of FEBRUARY for OPEN DATES!

There's something special about the kind of comfortable living afforded by this four bedroom, 2.5-bath, single-family home designated as "Lady Emma." The house takes its name from the street it inhabits, one of...

Kemp House

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

SPECIAL WINTER PRICING - NOW Through the end of FEBRUARY for OPEN DATES!

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...

La Prive

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

SPECIAL WINTER PRICING - NOW Through the end of FEBRUARY for OPEN DATES!

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...

Campbell Suite

Nightly and Weekly Rentals
1 Bedroom
1.5 Bathrooms
Comfortably Sleeps 2
Max Occupancy 2

SPECIAL WINTER PRICING - NOW Through the end of JANUARY!

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect...

Blackbeard's Treasure

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

SPECIAL MARCH & APRIL DISCOUNT! See Rate Table.

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...

Amelia by the Sea

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

SPECIAL MARCH & APRIL DISCOUNT! See Rate Table.

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...