Directory of Key West Vacation Rentals
Book your Key West accommodations now!
We encourage travelers, in order to avoid potential hazards, or scams targeting those searching for and booking online vacation home rentals in the Florida Keys, to seek out legitimate, licensed vacation rentals, which are listed on this website. Click here for helpful information on how to spot and avoid fraudulent offers, as well as better understand the guidelines legal vacation rentals must follow.
Staying in a Keys vacation home or condo rental is a great way to experience off-the-beaten-path neighborhoods and communities in our island paradise.
We urge visitors to be considerate and respect their neighbors. Since vacation rentals are typically located in residential communities, municipal or county noise ordinances apply. The same serenity and environmental qualities that attract visitors to the Keys are the reasons why many choose to live here on a year-round or part-time basis.
- KEYSCARIBBEAN RESORT VILLAS & MARINA
- 5950 Peninsula Avenue Key West FL 33040
- (305) 294-4676 E-mail Website
- Keys Coupon Available
- Featuring three luxury destinations in ideal Key West locations. Coral Hammock Resort Villas, King's Pointe Marina and Condos and a 3 bedroom, conch-style home in Truman Annex.
- 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.
- ROSE LANE VILLAS
- 522 Rose Ln Key West FL 33040
- (305) 292-2170 E-mail Website
- Green Lodging Pet-Friendly 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!
- SANTA MARIA SUITES RESORT
- 1401 Simonton Street Key West FL 33040
- (866) 726-8259 (305) 296-5678 E-mail Website
- 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!
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- Sun Outdoors Sugarloaf Key
- 311 Johnson Road Summerland Key FL 33042
- (305) 745-1079 Website
- Find paradise at Sun Outdoors Sugarloaf Key, located along a 7-acre saltwater lake, surrounded by state parks & mangroves. Stroll the lakefront boardwalk, cruise the lake on paddleboards & kayaks, or go explore our bike rental. Your perfect getaway awaits
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- THE CAPITANA KEY WEST
- 2401 N Roosevelt Blvd Key West FL 33040
- (305) 296-6925 E-mail Website
- Find your home away from home at the Capitana. Take your pick from spacious suites, private cottages, and guestrooms with furnished balconies overlooking the glimmering Gulf waters.
- Book now!
- VACATION HOMES OF KEY WEST
- 507 Whitehead St. Key West FL 33040
- (305) 294-7358 E-mail Website
- View video
- 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.
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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
- 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, and TV. Amenities plus! Take a peek!
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- CASA DEL SOL, a Key West Vacation
- Truman Annex/Old Town Key West Key West FL 33040
- (954) 345-4663 E-mail Website
- View video TripAdvisor
- Tropical 2BR/2.5BA Furnished Old Town/Truman Annex Vacation Townhome-Sleeps 6; Luxury 2 Story: Kitchen, Central Air, W/D, Private yard, Pool, Carport; 2 Blocks to Duval, Sunset & Beach. Call us today at 954-345-4663, and book your dream vacation!
- Book now!
- 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.
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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
- 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.
- HISTORIC HIDEAWAYS
- 1109 Duval St Key West FL 33040
- (800) 654-5131 (305) 294-RENT E-mail Website
- View video TripAdvisor
- An exceptional collection of Key West Vacation Rentals with private or shared pools. Private Homes, Cottages, Condos and Townhomes you are sure to love. Weekly-Monthly-Seasonally
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- HISTORIC KEY WEST VACATION RENTALS
- 1119 White Street Key West FL 33040
- (305) 296-1010 E-mail Website
- View video TripAdvisor
- Historic Key West Vacation Rentals - We provide the finest experience in vacation rentals to ensure your Key West vacation is one you will dream about for years after. "Stay a week ~ Stay a month ~ Stay a Lifetime"
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- KEY WEST HIDEAWAYS
- 1075 Duval St Ste C-11 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!
- Seaside Place
- 509 South Street Key West FL 33040
- (305) 393-6900
- Key West Seashell Cottage
- 719 Whitmarsh Lane Key West FL 33040
- (352) 871-2111