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Directory of Key West Vacation Rentals

Book your Key West accommodations now!

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  • KEY WEST HIDEAWAYS
  • 828 White Street Suite #3 Key West FL 33040
  • (305) 296-9090 E-mail Website
  • Pet-Friendly
  • Experience the unique charm of Key West with our one of-a-kind Vacation Rentals. When you want to escape the hustle & bustle of the real world, enjoy the perfect alternative to a pricey luxury hotel! With us you can book your own private Island getaway.
  • Book now!
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  • LAST KEY REALTY, INC.
  • 1121B Duval Street Key West FL 33040
  • (305) 292-6266 E-mail Website
  • Pet-Friendly Facebook Twitter
  • We want each of our guests to come away feeling that same magic we felt ourselves the first time we came to Key West. Our collection of 50+ meticulously furnished homes, condos & villas include 24/7 concierge guest services. Daily, Weekly & Monthly.
  • RENT KEY WEST VACATIONS - VACATION HOME RENTAL
  • 1075 Duval Street, Suite C11 Key West FL 33040
  • (800) 833-7368   (305) 294-0990 E-mail Website
  • Pet-Friendly
  • Why rent a private residence? Because you're smart and want the greatest value for your vacation dollar! We offer romantic hideaways, distinctive private Old Town residences and elegant waterfront condos to fit any lifestyle or budget.
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  • ROSE LANE VILLAS
  • 522 Rose Ln Key West FL 33040
  • (305) 292-2170 E-mail Website
  • Pet-Friendly Facebook TripAdvisor
  • The top rated 1, 2 and 3 bedroom pet-friendly vacation rentals feature modern amenities such as newly renovated kitchens, living rooms with flat screen TV's and free parking. Perfect for families, Rose Lane Villas are your home away from home.
  • Book now!
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  • SANTA MARIA SUITES RESORT
  • 1401 Simonton Street Key West FL 33040
  • (866) 726-8259   (305) 296-5678 E-mail Website
  • Facebook Twitter TripAdvisor
  • Recently renovated, luxurious 1 & 2 bedroom suites in Old Town. Steps to the ocean and Duval Street. Each suite features a full kitchen, living & laundry rooms and three 48" TV's. Amenities include complimentary beach access, happy hour, smoothies & more!
  • Book now!
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  • Susan's Key West Condo
  • Old Town Key West FL 33040
  • (740) 274-9091 E-mail Website
  • Watch our video Facebook
  • Susan provides everything needed for a fabulous vacation in historic Old Town. Beautiful decor with fully equipped kitchen, heated pool, off street parking, 2 bicycles, terrace balconies & internet. A quiet landing 2 blocks from the excitement of Duval St
  • Book now!
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  • THE CAPITANA KEY WEST
  • 2401 N Roosevelt Blvd Key West FL 33040
  • (305) 296-6925 E-mail Website
  • Facebook Instagram
  • Like having your own private home in the Keys with water views, enjoy easy-island living at its finest with two king bedrooms, premium amenities, and furnished decks along with a dedicated spa pool available exclusively for guests.
  • Book now!
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  • VACATION HOMES OF KEY WEST
  • 507 Whitehead St. Key West FL 33040
  • (305) 294-7358 E-mail Website
  • Watch our video Facebook Twitter
  • Browse our exclusive selection of properties including cottages, villas, condos & estates. Save time & money and book direct. Nightly, Weekly & Monthly vacation rentals that accommodate 1-22 guests. We are ready to help plan the perfect Key West vacation.
  • Book now!
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  • 1800 ATLANTIC/ALL FLORIDA KEYS PROPERTY MANAGEMENT
  • 1800 Atlantic Blvd. Key West FL 33040
  • (800) 433-2819   (305) 294-8877 E-mail Website
  • Facebook
  • Luxurious, oceanfront condos. Tropical garden complete with an Olympic size ocean front heated pool & sun deck, with an adjacent bubbling whirlpool. Three lighted tennis courts (one of which is clay) and racquetball courts. A unique barbecue/picnic area.
  • Book now!
  • AN ISLAND PARADISE VACATION CONDO
  • La Brisa Condominiums, Smathers Beach Key West FL 33040
  • (609) 822-8449 E-mail Website
  • OCEAN FRONT! Affordable luxury! Why not stay at our place? Spectacular 2 bedroom, 2 bath privately owned condo. Sleeps 4-6. Verandah "with a view to die for". Pool, Jacuzzi, Tennis, TV, VCR, CD player. Amenities plus! Take a peek!
  • Book now!
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  • AT HOME IN KEY WEST
  • 905 Truman Ave Key West FL 33040
  • (866) 304-2677   (305) 296-2594 E-mail Website
  • Facebook Instagram
  • From unequaled luxury surroundings to comfortably affordable accommodations, At Home in Key West has quality properties to suit your taste & budget. Our vacation specialists offer friendly professional & personalized service. We guarantee the best price.
  • Book now!
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  • CAYO HUESO RESORTS
  • 509 - 515 United St. Key West FL 33040
  • (305) 797-1500 E-mail Website
  • AWARD WINNING...Private 1, 2 & 3 bedroom bungalows, cottages & homes. Steps off Duval in Old Town & close to South Beach. Our resorts have a charming "conch" style with all imaginable amenities. Heated Pools, Full Kitchens, Sundecks, BBQ Grills & more.
  • Book now!
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  • DUVAL RETREAT - Contemporary DUVAL STREET Condo
  • 615 1/5 Duval St, Unit #1 Key West FL 33040
  • (305) 395-9056 E-mail Website
  • This NEWLY RENOVATED, contemporary 2b/1ba condo on DUVAL will give you a cozy escape while staying in the heart of Key West. Our location cannot be beat! Walking distance to all attractions, shopping and nightlife. Nightly and long-term rentals.
  • Book now!
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  • FLORIDA KEYS VACATION RENTALS, INC.
  • 1201 White Street, Suite 101 Key West FL 33040
  • (800) 598-7727   (305) 292-7424 E-mail Website
  • Facebook Twitter
  • Hundreds of homes, condos, townhomes & cottages located between Key Largo & Key West, most with waterfront locations. Preview them on our website & chat online or let our rental managers help you find your ideal vacation spot. Weekly & monthly rentals.
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  • Key West Seashell Cottage
  • 719 Whitmarsh Lane Key West FL 33040
  • (352) 871-2111
  • Seaside Place
  • 509 South Street Key West FL 33040
  • (305) 393-6900
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