Key West Vacation Rentals Filters Bedrooms 0+ 1+ 2+ 3+ 4+ 5+ 6+ 7+ 8+ 9+ 10+ 11+ Bathrooms 1+ 2+ 3+ 4+ 5+ 6+ 7+ Flexible Dates ? +/- 1 days +/- 2 days +/- 3 days Apply Filters Price Range: $0 - $10000 Amenities Air Conditioning Balcony BBQ Area Beach View Elevator Free Parking Hot Tub Pool Private Pool Wifi Type Apartment Condo Cottage House Townhouse Villa Guests Any 2 Adults 3 Adults 4 Adults 5 Adults 6 Adults 7 Adults 8 Adults 9 Adults 10 Adults 11 Adults 12 Adults 13 Adults 14 Adults 15 Adults 16 Adults 17 Adults 18 Adults 19 Adults 20 Adults 21 Adults 22 Adults Pet Friendly? 13-24 of 29 results Show122436 Sort byBedrooms - Low to HighBedrooms - High to Low Favorites Your Name: Your Email: Recipients Email: Enter one or more recipient email addresses separated by comma Message: Share MAP MANSION @ The Watson House 7 7 14 Key West From $1,525.00/night My Southernmost Kentucky Home 3 3 6 Key West From $200.00/night Pilar's Secret 3 2 8 Key West From $694.00/night Reynold's Retreat 3 3 6 Key West From $228.00/night South St. Cottage 2 2 4 Key West From $151.00/night Townhomes on Windsor #3 3 3.5 6 Key West From $850.00/night Townhomes on Windsor #4 3 3.5 6 Key West From $751.00/night Townhomes on Windsor #5 3 3.5 6 Key West From $750.00/night Townhomes on Windsor #6 3 3.5 6 Key West From $358.00/night Tucked Away - Main house 2 4 6 Key West From $250.00/night Tucked Away! 4 6 9 Key West From $400.00/night VILLA @ The Watson House 4 4 8 Key West From $750.00/night Prev123LastNext