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January 26th
5:31am · 75°F

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Key West ~ Vacation Penthouses

What Are Key West Penthouses? Penthouse are private apartment or condominium residences on the highest floors of a large renovated historic Victorian or modern condominium building with many luxurious high-end features. Key West penthouse properties have expansive porches, terraces, and /or decks offering unique viewing points of the island.

View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. or 305-294-7358 ext. 1

elegant key west tree house
special rates available

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Standard Rates: $3750 - $7350 per month

Overlooks large historic Meditation Garden
Quiet living
One Set of Stairs
Close to Higgs Beach

Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road in the exclusive Old Town Casa Marina neighborhood. With a wide wooden covered porch spanning the front of the house, every room still has the original casement windows providing a fabulous look-down view of different garden scenes.

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destination duval  a premier key west penthouse
special rates available

Mar 19- Mar 26
April 8 - Apr 17
Weekly $7900

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Standard Rates: $4130 - $10500 per week

4BR 4.5 BA - Sleeps 8
2450 SQ FT Premier 2-Level Penthouse
Uptown Duval Street Neighborhood
2 Private Covered Outdoor Porch Rooms
Shared Expansive Rooftop Deck and Heated Pool
Secured Covered Parking
Duval Square Vacation Rental

If you’re looking for a perfect Key West vacation rental that’s on Duval St, yet the ideal distance away from the bustle, you’re bound to love our– Destination Duval – A Premier Key West Penthouse. Strategically built on top of Duval Street, up here you’re in the cat bird’s seat, but at the same time invisible to the world below.

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heavenly hideout at rainbows end
special rates available

Feb 26- Mar 5
Weekly $5850

Mar 26 - Apr 2
Weekly $6400

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Standard Rates: $4195 - $9205 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool
Sun deck on ground level

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout Key West penthouse, you’re spot on, and you can do exactly that.


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