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4+ Bedroom Key West Rentals

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The Mermaid's Garden

Nightly and Weekly Rentals
4 Bedrooms
3 Full - 2 Half Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

END OF SUMMER DISCOUNT! 10% OFF already discounted prices for open dates AUGUST - SEPTEMBER 2017! Please call our office for details.

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...

Admiral's Lane

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

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 just blocks away, is Old...

Hermitage South

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

END OF SUMMER DISCOUNT! 10% OFF already discounted prices for open dates AUGUST - SEPTEMBER 2017! Please call our office for details.

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...

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...

Island Time

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

END OF SUMMER DISCOUNT! 10% OFF already discounted prices for open dates AUGUST - SEPTEMBER 2017! Please call our office for details.

Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident...

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...

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...