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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

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...

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...

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...

Paradise Grand

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

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 Key West. Copious...

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...