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Are you planning a Key West getaway to be spent in the lap of luxury? Or maybe you simply want to daydream about the island paradise. Look no further than our roundup of the most expansive and luxurious Key West vacation rentals. Ranging from updated conch cottages with picturesque front porches to palatial estates with private swimming pools and hot tubs, this small island has it all. Feast your eyes on these tropical sanctuaries.


Casa Royal

Available Through Preferred Properties

This beautifully updated hideaway boasts stainless steel appliances, granite countertops, skylights and modern bathrooms with a main house and pool cottage. This is sure to complete your chic Key West getaway.

1,536 square feet
4 Bedroom/3 Bath
Sleeps 8
Private Swimming Pool, Washer/Dryer, WiFi, Grill
Price Upon Request


Pineapple Cottage

Available Through Preferred Properties

Located just a block off Duval Street, this charming conch cottage features a beautifully landscaped back deck with private swimming pool and tropical-colonial décor.

2,000 square feet
2 Bedroom/2 Bath
Sleeps 4
Private Swimming Pool, Parking, Gated Property, WiFi, Washer/Dryer, Grill
Price Upon Request


Frangipani on Von Phister

Available Through Preferred Properties

With beautiful marble and limestone slab flooring, updated furniture, a tropical pool and spacious upstairs balcony, the Frangipani on Von Phister is all luxury.

2,121 square feet
3 Bedroom/3 Bath
Sleeps 6
Private Swimming Pool, Gated Property, Washer/Dryer, WiFi, Tennis Rackets, Grill, Parking, Outdoor Shower, Balcony
Price Upon Request


Conch Heaven

Available Through Preferred Properties

Located in the heart of Old Town, this spacious conch cottage features a wraparound porch, four poster beds and beautiful hardwood floors for a luxurious retreat.


4,284 square feet
5 Bedroom/5 Bath
Sleeps 10
Private Swimming Pool, WiFi, Washer/Dryer, Parking
Price Upon Request

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