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Directory of Key West Vacation Rentals

The Keys offer numerous opportunities to rent private homes or condominiums. In many cases, local regulations require the homeowner to have a special vacation rental or short-term rental permit. Please check with your rental agent or homeowner for any restrictions that might apply in the area of the Keys you wish to stay.

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1800 ATLANTIC/ALL FLORIDA KEYS PROPERTY MANAGEMENT
1800 ATLANTIC/ALL FLORIDA KEYS PROPERTY MANAGEMENT
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Phone: 305-294-8877 *  Toll Free: 800-433-2819 *  Fax: 305-294-7356
Email: info@1800atlantic.com
1800 Atlantic Blvd.
Key West ,  FL  33040

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.
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A-1 BEACH RENTALS OF KEY WEST (By Owner)
Phone: 305 295-0049 *  Toll Free: 1 800-458-6555 * 
Email: kwparadisefound@yahoo.com
Key West ,  FL  33040
Located on the Atlantic Ocean-Deluxe 1-3 Bed Condos furnished Key West style. A/C, fully equipped kitchen,cable TVs,Stereo, Jacuzzi (Master Bath), Olympic size oceanfront pool & spa, Tennis courts, BBQ/Picnic Area. Set in a Tropical Beachfront Paradise!

AN ISLAND PARADISE VACATION CONDO
Phone: 609-822-8449 * 
Email: richardgober@comcast.net
La Brisa Condominiums, Smathers Beach
Key West ,  FL  33040
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!

AT HOME IN KEY WEST
AT HOME IN KEY WEST
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Toll Free: (866) 304-2677 * 
Email: reservations@athomekeywest.com
905 Truman Ave
Key West ,  FL  33040

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
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ATLANTIS HOUSE  Click for map
Book Now   
Phone: (305) 292-1532 * 
Email: info@atlantishouse.com
1401 Atlantic Boulevard
Key West ,  FL  33040
A private, romantic retreat with only 2 suites, ideal for honeymoons & anniversaries along Key West's beaches. Free bicycle use, WiFi, and Parking. Owners Capt. Steve & Kayla offer fishing charters, ecotours & snorkeling trips.

CASA DEL SOL, a Key West Vacation
CASA DEL SOL, a Key West Vacation
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Phone: 954-345-HOME (4663) * 
Email: MiamiToKeyWest@bellsouth.net
Truman Annex/Old Town Key West
Key West ,  FL  33040

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 at 954-345-HOME(4663).View our South Beach/Miami Beach rental!
View Reviews on Trip Advisor    Book Now   

CASA ROSA - PRIVATE RENTAL HOME
Phone: 1.800.875.4555 * 
Email: dolphinvacations@aol.com
Old Town
Key West ,  FL  33040
Spacious 4 Bedroom, 4 Bath. Private pool & Jacuzzi. Historic Eyebrow home in popular Historic Seaport district in Old Town, just one block from the world famous Duval Street, a few blocks to Mallory Square. Visit: http://www.dolphinvacations.com.

CAYO HUESO RESORTS
CAYO HUESO RESORTS
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Phone: (305) 797-1500 *  Fax: (305) 294-5973
Email: info@cayohuesoresorts.com
509 - 515 United St.
Key West ,  FL  33040

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.

CHAVEZ HOUSES & GARDEN COTTAGE Circa 1870
CHAVEZ HOUSES & GARDEN COTTAGE  Circa 1870
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Phone: 305-296-7893 * 
Email: villaskeywest@gmail.com
522 Margaret Street
Key West ,  FL  33040

Sleeps 8 plus 6 for total of 14. Rent together or separately. Heart of Old Town. 2 doors to Michael's Restaurant, 400 ft to historic city cemetery, 600 ft to seafront Historic Boardwalk. Lush plantings. Quiet, island, tropical - real Key West
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DOUG MAYBERRY - Key West Homes for Rent
DOUG MAYBERRY - Key West Homes for Rent
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Phone: 305-292-6157 * 
Email: rentals@dougmayberry.com
1075 Duval Street
Suite C23
Key West ,  FL  33040

Experience the tropical lifestyle in a relaxed, private Key West home. Our exclusive collection of homes is carefully selected so that you can experience the highest standards, thoughtful amenities & gracious hospitality. Enjoy our concierge service too!

FLORIDA KEYS LUXURY VACATION RENTALS - Premier Vacation Rentals
This property is Pet Friendly   
Phone: 305-853-8700 *  Toll Free: 877-FLAKEYS 352-5397 * 
Email: jane@floridakeysluxuryvacationrentals.com
Key West ,  FL  33040
Specializing in upscale waterfront homes and elite properties, we set the standard for quality of inventory, depth of experience, extraordinary local knowledge, island hospitality - and attentive, innovative, friendly service.

FLORIDA KEYS REALTY, Inc.
Phone: (305) 745-3717 *  Toll Free: (800) 277-7756 *  Fax: (305) 745-7377
Email: info@floridakeysrealty.com
P.O. Box 421177
Summerland Key ,  FL  33042
The Florida Keys has overwhelming sunsets, crystal green & blue waters & coconut palms swaying in the warm trade winds. At Florida Keys Realty we specialize in finding the perfect place for your stay in the Florida Keys & Making Your Dreams Come True!

FLORIDA KEYS VACATION RENTALS, INC.
Phone: 305-292-7424 *  Toll Free: 1-800-598-7727 * 
Email: customercare@RentalsFloridaKeys.com
1201 White Street, Suite 101
Key West ,  FL  33040
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
HISTORIC HIDEAWAYS
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Phone: 305-294-RENT *  Toll Free: 800-654-5131 *  Fax: 305-294-8632
Email: rentals@HistoricHideaways.com
1109 Duval St
Key West ,  FL  33040

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
View Reviews on Trip Advisor    Book Now   

HYATT WINDWARD POINTE, A HYATT VACATION CLUB
Phone: 305-293-5050 *  Toll Free: 1-800-926-4447 *  Fax: 305-293-5051
Email: info@spottswood.com
3675 South Roosevelt Boulevard
Key West ,  FL  33040
Comfortably appointed Two Bedroom/Bathroom Units with King-Sized Beds in Master Suite. Accommodates 6 people. TV/VCR/DVD/Stereo/CD Player. Fully Equipped Kitchens with Separate Dining Rooms.

KEY WEST BY THE SEA RENTALS AND SALES
Phone: 305-294-6069 *  Fax: 305-293-8052
Email: gshepard@bellsouth.net
P.O. Box 5515
Key West ,  FL  33045
Gale Shepard, Broker offers SEASONAL RENTALS in many one, two and three bedroom fully equipped condominiums and VARIOUS LENGTH LEASES (furnished and unfurnished) around Key West. Most are on beautiful Smathers Beach. I also SELL Key West real estate!

KEY WEST VACATION RENTALS
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KEY WEST ,  FL
With FlipKey's selection of over 400 vacation rental homes, villas, condos, and beach houses, finding lodging in Key West has never been easier. Check out FlipKey for amazing value on vacation rental accommodations in the Floriday Keys.

KEYSCARIBBEAN RESORT VILLAS & MARINA
Keys Coupon   
Phone: 305-294-4676 * 
Email: res@keyscaribbean.com
5950 Peninsula Avenue
Key West ,  FL  33040
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.

KOKOMO CONDO: By Owner
KOKOMO CONDO: By Owner
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Phone: (847) 696-3900 * 
Email: marie.smith@comcast.net
1901 S Roosevelt Blvd
Key West ,  FL  33040

A beautiful 2/2 across from Smathers Beach sleeps 6. Gorgeous ocean view Unit is equipped like home. Frequently updated Specials on Kokomo's website. Fully licensed for transient rentals Gated condominium. Heated pool, Jacuzzi, Tennis court, Saunas.

LAST KEY REALTY, INC.
LAST KEY REALTY, INC.
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Phone: 305-292-6266 *  Fax: 866-913-9302
Email: alex@lastkeyrealty.com
1121B Duval Street
Key West ,  FL  33040

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.
This property is Pet Friendly   

PARROT KEY HOTEL AND RESORT
PARROT KEY HOTEL AND RESORT
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Phone: 855-462-0807 *  Fax: 305-292-3322
Email: info@parrotkeyresort.com
2801 N. Roosevelt Boulevard
Key West ,  FL  33040

WEEKDAY SALE: Save up to 15% when staying Sunday - Thursday! Call 855-462-0807 or visit www.parrotkeyresort.com. Family friendly 1 & 2 bedroom suites & waterview guest rooms. Enjoy 4 pools, dining & lush gardens. 'Top 3 Luxury Resort' on TripAdvisor
View Reviews on Trip Advisor    Book Now   

RENT KEY WEST VACATIONS - VACATION HOME RENTAL
This property is Pet Friendly   
Phone: 1-305-294-0990 *  Toll Free: 1-800-833-7368 *  Fax: 1-305-292-3723
Email: info@rentkeywest.com
1075 Duval Street, Suite C11
Key West ,  FL  33040
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
ROSE LANE VILLAS
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Phone: 305-292-2170 * 
Email: info@roselanevillas.com
511 Eaton Street
Key West ,  FL  33040

Located in the heart of Old Town, The Villas was recognized by the Miami Herald as the Keys "Best Value Hotel." Living rooms, kitchens, pool and parking are only some amenities of our 1, 2 and 3 bedroom Villas. Great value. Great location. Great vacation.
View Reviews on Trip Advisor    This property is a Florida Green Lodging Certified Property This property is Pet Friendly    Book Now   

SANTA MARIA SUITES RESORT
Book Now   
Phone: 305-296-5678 *  Toll Free: 866-726-8259 *  Fax: 302-296-2519
Email: info@santamariasuites.com
1401 Simonton Street
Key West ,  FL  33040
New Luxury 2BR, 2BA Suites in Old Town Key West. Steps to the ocean and Duval Street. ALL of the amenities you expect and desire. Relaxation, comfort, and stylish appointments to make this private resort a place to entertain, to get away or to dream.

SERENDIPITY CONDOMINIUM IN KEY WEST
Phone: 443-373-9561 *  Fax: 410-289-8526
Email: serendipitynkeys@aol.com
La Brisa Condominiums
Key West ,  FL  33040
We offer 3, 2 or 3 bedroom condos in La Brisa@Smathers Beach. Ultra deluxe and affordably priced. From granite counters to spectacular views, we're the best deal on the beach!

TRUMAN ANNEX VACATIONS / KEY WEST GOLF CLUB
Phone: (305)292-1881 *  Toll Free: 888-721-7368 *  Fax: (305)292-7822
Email: rentals@compass-realty.com
Truman Annex Real Estate Co.
Key West ,  FL  33040
Experience Key West's premier waterfront and golf course communities. From luxurious oceanfront condominiums to "conch style" townhouses on the fairways, we have the properties to fit any vacation budget. Free brochure.

VACATION HOMES OF KEY WEST
VACATION HOMES OF KEY WEST
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Phone: (305)294-7358 * 
Email: info@vhkw.com
Key West ,  FL  33040

Our property picks some of the most beautiful vacation cottages, homes and townhomes. Architectural styles range from Adorable Caribbean Cottages to Hidden Courtyard Poolside Villas and Spacious and Luxurious Private 4 and 5 bedroom Victorian Homes.

VACATION RENTALS IN KEY WEST
Book Now   
KEY WEST ,  FL
With FlipKey's selection of over 400 vacation rental homes, villas, condos, and beach houses, finding lodging in Key West has never been easier. Check out FlipKey for amazing value on vacation rental accommodations in the Floriday Keys.

YOUR CONDO BY THE BEACH
Phone: (305) 393 7513 * 
Email: Pam@keywestbreeze.com
La Brisa Condominiums, Smathers Beach
Key West ,  FL  33040
ENJOY the beach by day and Old Town by night. VIEW turquoise waters and swaying palms from your balcony. 1 bedroom/1 bath condo is perfect for one romantic couple or a small family. Fully equipped from blender to beach towels. Pool, Tennis, WiFi.

CASA ALANTE GUEST COTTAGES
Phone: (305) 293-0702
1435 S. Roosevelt Blvd
Key West ,  FL  33040

LAZY LANE COTTAGES
Phone: 877-413-5299
719 Whitmarsh Lane
Key West ,  FL  33040

ROSE LANE VILLAS
Phone: (800) 294-2170
522-524 Rose Lane
Key West ,  FL  33040

SEASIDE PLACE
Phone: 305-393-6900
509 South Street
Key West ,  FL  33040

TRUMAN ANNEX "HEMINGWAY'S HIDEAWAY"
Phone: 205-281-4773
The Foundry
101 Front Street, Unit 21
Key West ,  FL  33040

A KEY RETREAT
Phone: 305-296-0011
Key West ,  FL  33040

A PARADISE RENTAL - BY OWNER IN KEY WEST
Phone: (440)796-3778
Key West ,  FL  33040