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Island Wind Windward Park Swimming Pool
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Key West Townhouse
2 BR / 2.5 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
Dishwasher • Microwave • Washer/Dryer
ISLAND WIND: 2 bedroom, 2 bath Bahamian- style townhome, with tin roof and white spindled decks. Snuggle into an oh- so- comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs...
The Lion's Paw is a Catalina Morgan 440 with two cabins, two heads.
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Key West Yacht
2 BR / 2 BA / Sleeps 4 2 4 3 night min stay
Yacht / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
Microwave • Washer/Dryer • Air Conditioning
Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half da...
Key West Florida Vacation Rentals - Condo
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Key West Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jum...
(1) Excellent (1 review)
Pool
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Key West Cottage
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Cottage / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Washer/Dryer
Daily price varies by season, and length of stay. Range of prices shown above. Private compound right in the heart of old town. 1 minute or less from Schooner Wharf with all the water activities imaginable; Sloppy Joe'...
(12) Excellent (12 reviews)
Living Room with 42" SONY LED, BOSE surround sound and screened deck
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Key West Condo
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Tee By The Sea" Vacation Rental (we Include 7 Bikes Free For Our Guests! ! ! ) If You Love... Golf, Sport Fishing/boating, Art/theater And Fantastic Live Entertainment... Than You'll Love "tee By The Sea". We're ...
(4) Excellent (4 reviews)
Key West Florida Vacation Rentals - Villa
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Key West Villa
6 BR / 7 BA / Sleeps 16 6 16 7 night min stay
Villa / 6 Bedrooms / Sleeps 16
6 bedrooms 7 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven ...
(2) Excellent (2 reviews)
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Key West Villa
5 BR / 5.5 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off- street...
(3) Excellent (3 reviews)
Pool, Spa and Sunshade Area
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Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This is a non- smoking condo (you may smoke on the balcony only) with that "home away from home" comfortable appeal. My condo is reasonably priced and includes 2 bedrooms (1 king in the master suite/1 queen in the guest ...
(55) Excellent (55 reviews)
Key West Florida Vacation Rentals - Guesthouse
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Key West Guesthouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Guesthouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from a...
(3) Excellent (3 reviews)
Key West Florida Vacation Rentals - Home
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Key West Home
3 BR / 2.5 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid- century Florida home with dramatic Caribbean design, has created an ideal contemporary "Floribbean" style villa in the Casa Marina di...
(2) Excellent (2 reviews)
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Key West Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Please Call/email For Availability As We Do Not Use The Calendar Shown Casa Rosa Is A Four Bedroom, Four Bath Classic "eyebrow" Style Home Located In Historic Old Town Key West. This Home Is Just 1 Block Off Duval S...
(4) Excellent (4 reviews)
Key West Florida Vacation Rentals - Home
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Key West Home
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
AMELIA HOME - A 2 bedroom 2. 5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been ...
(2) Excellent (2 reviews)
Key West Florida Vacation Rentals - Condo
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Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 2 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island par...
(53) Excellent (53 reviews)
Key West Florida Vacation Rentals - Townhouse
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Key West Townhouse
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have b...
(2) Excellent (2 reviews)
Key West Florida Vacation Rentals - Home
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Key West Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a recently renovated private home with three bedrooms and two baths located in a quiet, Old Town, Key West neighbor...
(1) Excellent (1 review)
Key West Florida Vacation Rentals - Townhouse
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Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local gall...
(6) Excellent (6 reviews)
Key West Florida Vacation Rentals - Cottage
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Key West Cottage
1 BR / 1.5 BA / Sleeps 4 1 4 Min stay varies
Cottage / 1 Bedroom / Sleeps 4
1 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give...
(3) Excellent (3 reviews)
Key West Florida Vacation Rentals - Villa
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Key West Villa
1 BR / 1 BA / Sleeps 2 1 2 7 night min stay
Villa / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Dishwasher • Microwave
PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away fro...
(2) Excellent (2 reviews)
first floor great room
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Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill...
(15) Excellent (15 reviews)
Key West Florida Vacation Rentals - Condo
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Key West Condo
2 BR / 1 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
This is a brand new listing to VHR! The Shabby Chicken along with my attention to detail and welcoming our guest has earned over 25 5- STAR ratings (Listed with another vacation site). Be sure to read our guests' fantas...
(5) Excellent (5 reviews)
Key West Florida Vacation Rentals - Home
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Key West Home
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Ahoy! PirateHead Cove, your affordable vacation dream- come- true is now taking bookings for 2016- 17! Max occupancy: 2 couples or 1 couple with up to 3 children under 12. The calendar on this site shows availab...
(10) Excellent (10 reviews)
Key West Florida Vacation Rentals - Condo
1 / 1

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 2 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Decorator furnished two bedroom, two full bath condo in Key West, Florida. Only a five minute drive to Key West's largest beach - Smather's Beach. Full kitchen, three flat screen TV's, outside porch overlooking ...
(1) Excellent (1 review)
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Key West Townhouse
3 BR / 3 BA / Sleeps 6 3 6 3 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Coastal on Coral is located in the beautiful gated community of Coral Hammock on the Quiet end of Key West on Stock Island. This home has all the amenities of a house and a resort combined boasting 3 bedrooms, all with ...
(1) Excellent (1 review)
Key West Florida Vacation Rentals - Townhouse
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Key West Townhouse
2 BR / 2 BA / Sleeps 4 2 4 30 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Nestled behind hisbiscus and stands of bamboo Lone Palm welcomes you to a tropical oasis in the heart of Old Town. Located just a block off Duval at the corner of Truman & Simonton in Windward Park a gated community cons...
(9) Excellent (9 reviews)
Key West Florida Vacation Rentals - Apartment
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Key West Apartment
1 BR / 1 BA / Sleeps 4 1 4 30 night min stay
Apartment / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • Washer/Dryer
You are home at the Signpost, at the property edge. Tropical apartment: 1 Bedroom, 1 bath, large and roomy spaces; private deck, washer/dryer enclosed on deck. Walking distance to all the attractions, neighborhood ...
Key West Florida Vacation Rentals - Condo
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Key West Condo
2 BR / 1 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
This is a brand new listing to VHR! We are running a JUNE SPECIAL DISCOUNT! ! The Rooster Retreat along with my attention to detail and welcoming our guest has earned over 30 5- STAR ratings (Listed with another vaca...
(2) Excellent (2 reviews)
Key West Florida Vacation Rentals - Townhouse
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Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
CORAL GARDEN: A 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kit...
(4) Excellent (4 reviews)
Key West Florida Vacation Rentals - Home
1 / 3

Key West Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Air Conditioning
Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. You take over the full house, deck, balcony, large living- room, kitchen, garden and the best part, the king- bedro...
Key West Florida Vacation Rentals - Townhouse
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Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
KEY WEST FOUND - A striking 2 bedroom, 2. 5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room fu...
(2) Excellent (2 reviews)
Key West Florida Vacation Rentals - Condo
1 / 31

Key West Condo
3 BR / 2 BA / Sleeps 8 3 8 30 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
I rent starting the first of the month till the end of the month, or longer. We do not rent daily or for one or two weeks due to licencing limitations, but you do have options... Once you pay the monthly rate, you hav...
(1) Excellent (1 review)
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About Key West

A laid-back city in the Florida Keys, Key West should be on every traveler's vacation list. With equal parts nature, history, and nightlife, this Florida destination has a little something for everyone.


A Short History of Key West

At the very end of the Florida Keys, this four-square-mile island was first settled by Spanish explorers led by Ponce de León. The remote location was sparsely populated until it was claimed by the United States in the early 19th century. By the turn of the 20th century, Key West was actually the largest and most moneyed city in Florida, thanks to its quick development, naval base, and cigar industry. The locale began to develop its reputation as a tourist hotspot around that time, and this southernmost U.S. city still holds that identity today.


What Key West Does Best

This small island is packed with attractions and activities. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street, the center of Key West’s nightlife scene.


Natural Beauty

Key West isn’t known for its beaches, but Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset. Explore the waters around Key West by sailboat, kayak, or sunset cruise to get a closer look at the sparkling gulf. For a unique adventure, head 70 miles offshore to Dry Tortugas National Park. Explore Fort Jefferson, the coral reefs, and the island’s impressive variety of wildlife and tropical plants.
 

Historical Markers

To get a quick look at everything Key West has to offer, hop on the Conch Tour Train. You’ll get an earful of the area’s past, along with a little local trivia. When you’re ready to dig in, make the Ernest Hemingway Home & Museum your first stop. Here you can learn more about the famous writer’s life and see where he penned some of his best selling novels.

Don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Today the house is both a museum and a political retreat, and it’s well worth a visit.
 

Vibrant Nightlife

No trip to Key West is complete without a night out on the town, and options range from family-friendly to wildly theatrical. Take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views. For some grownup fun, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse. Finish the night off with a drink at the Green Parrot, Key West’s oldest bar, or Sloppy Joe’s, one of Hemingway’s favorite hangouts.

Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere. One night here isn’t enough, so book a vacation home and stay awhile on this island destination.