Key West Penthouses - 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.
Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.
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Sept 19 - Sept 28
Oct 1- Oct 5
Oct 8- Oct 12
Oct 28- Nov 1
Standard Rates: $3500 - $6825 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.
Standard Rates: $3800 - $5750 per month
Overlooks large historic Meditation Garden
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.
Sept 30- Oct 4
Nov 24- Dec 1
Dec 15- Dec 19
Standard Rates: $2900 - $6100 per week
4BR 4BA + (2 1/2 BA) - Sleeps 8
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.
Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location! Mallory Square and the beach.