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4+ Bedroom Key West Rentals

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The Mermaid's Garden

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

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 installed in a garden bursting with tropical...

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Island Style

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

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 it all: 2,000 square feet in a compact two-story format, porches and balconies,...

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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...

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Truman House

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

The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly...

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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...

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Lady Emma

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

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 the most desirable addresses in town. It's part of Truman Annex, an award-winning...

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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...

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The Sanctuary

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

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 shower. Five doors of...

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