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The Mermaid's Garden

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

DISCOUNTED RATES for Open Dates this FALL!

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 brass mermaid sculpture...

Admiral's Lane

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

DISCOUNTED RATES for Open Dates this FALL!

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...

Banana Key

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED RATES for Open Dates this FALL!

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...

La Prive

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

DISCOUNTED RATES for Open Dates this FALL!

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...

The Courtyard

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

DISCOUNTED RATES for Open Dates this FALL!

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...

Royal Palm

Nightly and Weekly Rentals
2 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED RATES for Open Dates this FALL!

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this...

Rose Treehouse

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

DISCOUNTED RATES for Open Dates this FALL!

Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole...

Campbell Cottage

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

DISCOUNTED FALL RATES!

Campbell Cottage is the perfect place for living large in an intimate, comfortable one bedroom/one bath cottage. A locked privacy fence surrounds the lushly landscaped Campbell Court compound, which has an enticing Monaco pool at its center. You can step off your front...

Hilltop Hideaway

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

DISCOUNTED FALL RATES!

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 condo is...

La Hacienda

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

DISCOUNTED FALL RATES!

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...

la Palm d'or

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

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 feathery palms, creating a perfectly secluded oasis...

Azure Hideaway

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

DISCOUNTED FALL RATES!

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 Hideaway could...

Blackbeard's Treasure

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

DISCOUNTED FALL 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. The 1950's era...

Ultimate Pool Cottage

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

DISCOUNTED FALL RATES!

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. Like...

Hemingway's Library

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

DISCOUNTED FALL RATES!

This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books,...

Paradise Grand

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

DISCOUNTED FALL RATES!

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 island of...