Key West Vacation Rentals Filters Bedrooms 0+ 1+ 2+ 3+ 4+ 5+ 6+ 7+ 8+ 9+ 10+ 11+ 12+ Bathrooms 1+ 2+ 3+ 4+ 5+ 6+ 7+ 8+ 9+ 10+ 11+ Flexible Dates ? +/- 1 days +/- 2 days +/- 3 days Apply Filters Price Range: $0 - $100000 Total trip price, includes all fees Amenities Air Conditioning Balcony BBQ Area Beach View Elevator Free Parking Hot Tub Ocean View Pool Private Pool Wifi Type Apartment Condo Cottage Duplex House Studio 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 23 Adults 24 Adults 25 Adults 26 Adults 27 Adults 28 Adults 29 Adults 30 Adults Pet Friendly? 1-127 of 127 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 Poolside Paradise @ Tropical Village 0 1 2 Key West Choose dates to calculate price Treetop Studio @ Eyebrow House 0 1 4 Key West Choose dates to calculate price Harveys Haven 0 1 2 Key West Choose dates to calculate price Matisse Studio @ the Galleria 0 1 2 Key West Choose dates to calculate price Osprey @ Colony 0 1 4 Key West Choose dates to calculate price Bali Hideaway 0 1 2 Key West Choose dates to calculate price Casa Atlantica Studio 1 1 2 Key West Choose dates to calculate price Casa Atlantica One Bedroom 1 1 2 Key West Choose dates to calculate price Hidden Oasis @ Colony 1 1 4 Key West Choose dates to calculate price Sunset Suite @ Colony 1 1 4 Key West Choose dates to calculate price Namaste 1 2 2 Key West Choose dates to calculate price Ann Street Cottage 1 1.5 2 Key West Choose dates to calculate price Tranquility On Ann Street 1 1 2 Key West Choose dates to calculate price Colony Calypso 1 1 4 Key West Choose dates to calculate price Colony Poolside 1 1 2 Key West Choose dates to calculate price La Casa Cubana 1 1.5 6 Key West Choose dates to calculate price Orange Blossom Suite @ Conch Republic Cottage 1 1 4 Key West Choose dates to calculate price Olivia's Landing 1 1 2 Key West Choose dates to calculate price Deckside Suite @ Conch Republic Cottage 1 1 2 Key West Choose dates to calculate price Porchside Paradise @ Conch Republic Cottage 1 1 4 Key West Choose dates to calculate price Bonaire Suite 1 1.5 4 Key West Choose dates to calculate price La Casa de Luna 1 1 4 Key West Choose dates to calculate price Olivia's Nest 1 1 4 Key West Choose dates to calculate price Mango Hideaway @ Eyebrow House 1 1 3 Key West Choose dates to calculate price Orchid Suite 1 1.5 4 Key West Choose dates to calculate price Island Style @ Colony 1 1 4 Key West Choose dates to calculate price Esperanza Suite 1 2 4 Key West Choose dates to calculate price Poolside Hide-Away @ Palm Gardens 1 1 4 Key West Choose dates to calculate price Watson House Grand Estate 11 11 22 Key West Choose dates to calculate price Tropical Village 12 9 30 Key West Choose dates to calculate price Secret Courtyard 2 1 4 Key West Choose dates to calculate price Glimmer Glass @ KW Beach Club 2 2 4 Key West Choose dates to calculate price Margaret Street Retreat 2 2 6 Key West Choose dates to calculate price Beach Club Tranquil Seas #107 2 2 4 Key West Choose dates to calculate price Starfish 2 2 6 Key West Choose dates to calculate price Pineapple Cottage 2 1.5 4 Key West Choose dates to calculate price Paradise Found 2 2 4 Key West Choose dates to calculate price Casa Bonita @ Duval Square 2 2.5 6 Key West Choose dates to calculate price Utopia @ Tropical Village 2 1 4 Key West Choose dates to calculate price Key Lime Cottage 2 3 4 Key West Choose dates to calculate price Windward Breeze 2 2 4 Key West Choose dates to calculate price A Caribbean Alternative 2 2.5 4 Key West Choose dates to calculate price Eyebrow Suite @ Eyebrow House 2 1.5 4 Key West Choose dates to calculate price Thalias Retreat 2 2.5 6 Key West Choose dates to calculate price Conch Easy Livin' 2 3 6 Key West Choose dates to calculate price Knot a Worry 2 2.5 6 Key West Choose dates to calculate price Beach Club Siesta #104 2 2 6 Key West Choose dates to calculate price Beach Club Seabreeze #103 2 2 5 Key West Choose dates to calculate price Beach Club Sunrise #112 2 2 5 Key West Choose dates to calculate price Beach Club Oasis #304 2 2 4 Key West Choose dates to calculate price A Windsong Delight 2 2.5 4 Key West Choose dates to calculate price Key West Crown Jewel 2 2 6 Key West Choose dates to calculate price Paradise Place @ Duval Square 2 2.5 6 Key West Choose dates to calculate price Artist Condo @ Duval Square #7 2 2.5 6 Key West Choose dates to calculate price Villa Serena @ Duval Square 2 2.5 4 Key West Choose dates to calculate price CasaBella @ Duval Square 2 2.5 6 Key West Choose dates to calculate price Duval Square Delight 2 2.5 4 Key West Choose dates to calculate price Duval Square Retreat 2 2.5 4 Key West Choose dates to calculate price Hidden Treasure @ Colony 2 2 6 Key West Choose dates to calculate price La Brisa #303W 2 2 4 Key West Choose dates to calculate price Ocean Vista 403E @ La Brisa 2 2 4 Key West Choose dates to calculate price Sea Orchid @ La Brisa 405E 2 2 4 Key West Choose dates to calculate price A Slice of Paradise -Shipyard Palms 2 1.5 4 Key West Choose dates to calculate price Tiki Beach Too 2 2 6 Key West Choose dates to calculate price Ashe Splashe 2 3 6 Key West Choose dates to calculate price Escape on Fleming 2 1 4 Key West Choose dates to calculate price South St. Cottage 2 2 4 Key West Choose dates to calculate price Rum Cay @ Sunrise Suites 2 2 6 Key West Choose dates to calculate price Parrotville 2 2 4 Key West Choose dates to calculate price Sunrise Suite 203 2 2 6 Key West Choose dates to calculate price Havana Lane 2 2 4 Key West Choose dates to calculate price Paradise on Porter 2 2.5 4 Key West Choose dates to calculate price Cuban Paradise @ Cuban Club 2 2 6 Key West Choose dates to calculate price Petes West Cottage 2 1 4 Key West Choose dates to calculate price Petes East Cottage 2 1 4 Key West Choose dates to calculate price Tropical Hideaway @ Tropical Village 2 1 4 Key West Choose dates to calculate price Tropical Cottage @ Tropical Village 2 2 5 Key West Choose dates to calculate price Catherine House 2 2 4 Key West Choose dates to calculate price The Southern Cross @ Tropical Village 2 2 6 Key West Choose dates to calculate price Fleming-O 2 1 6 Key West Choose dates to calculate price La Casa de Luces 2 2 4 Key West Choose dates to calculate price A Cuban Club Suite 2 2 8 Key West Choose dates to calculate price Vista Fresco 2 2 6 Key West Choose dates to calculate price Toon Hall @ Tropical Village 3 2 10 Key West Choose dates to calculate price Absolutely Paradise 3 2.5 8 Key West Choose dates to calculate price Bahama Breeze 3 3.5 6 Key West Choose dates to calculate price Beach Club Paradise Penthouse #401 3 3 6 Key West Choose dates to calculate price Windsor Townhomes #6 3 3.5 6 Key West Choose dates to calculate price Reynolds Retreat 3 3 6 Key West Choose dates to calculate price Villa de Palmas 3 3 6 Key West Choose dates to calculate price Villa Paradiso 3 3 6 Key West Choose dates to calculate price Louisas Hideaway 3 3 6 Key West Choose dates to calculate price Elizabeth Retreat 3 2 6 Key West Choose dates to calculate price Casa de Cuba 3 2 6 Key West Choose dates to calculate price Coconut Cabana 3 2 6 Key West Choose dates to calculate price Colony Conch Casa 3 2.5 6 Key West Choose dates to calculate price Bahama Dreams 3 2 6 Key West Choose dates to calculate price Duval Square Courtyard Condo 31 3 2 8 Key West Choose dates to calculate price Windsor Townhomes #3 3 3.5 6 Key West Choose dates to calculate price Windsor Townhomes #4 3 3.5 6 Key West Choose dates to calculate price Windsor Townhomes #5 3 3.5 6 Key West Choose dates to calculate price Beach Club Shangra La #206 3 2 6 Key West Choose dates to calculate price Higgs Beach Hideaway 3 2 8 Key West Choose dates to calculate price Key West Conch 3 4.5 6 Key West Choose dates to calculate price Sans Souci 3 2.5 7 Key West Choose dates to calculate price Casa Lima 3 2 6 Key West Choose dates to calculate price Casa Amor 3 2.5 8 Key West Choose dates to calculate price Casa Loca 3 2.5 8 Key West Choose dates to calculate price Casa Margarita 3 3 8 Key West Choose dates to calculate price Mango Cottage 3 2 6 Key West Choose dates to calculate price A Bit of Heaven 3 3 6 Key West Choose dates to calculate price Soleil Chalet 3 3 8 Key West Choose dates to calculate price Royal Escape 3 3 10 Key West Choose dates to calculate price Tobago House 3 3 6 Key West Choose dates to calculate price Royal Haven 3 2 6 Key West Choose dates to calculate price Tiki Beach - Big Pine Key 4 3 10 Big Pine Key Choose dates to calculate price Aloha 4 4 10 Key West Choose dates to calculate price Ole' Olivia 4 3.5 8 Key West Choose dates to calculate price Casa Blanca 4 3 8 Key West Choose dates to calculate price VILLA @ The Watson House 4 4 8 Key West Choose dates to calculate price Louisa House 4 3.5 8 Key West Choose dates to calculate price Duval Square Penthouse 4 4.5 10 Key West Choose dates to calculate price Petes Cottages 4 2 8 Key West Choose dates to calculate price Casa Caribe 4 4 8 Key West Choose dates to calculate price Villa Bella 5 4 12 Key West Choose dates to calculate price Ceasar's Paradise 5 5.5 10 Key West Choose dates to calculate price MANSION @ The Watson House 7 7 14 Key West Choose dates to calculate price Prev1LastNext