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House Rentals and Apartments in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    6 Bedrooms / 6 Bathrooms / Sleeps 24
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    6 Bedrooms / 5 Bathrooms / Sleeps 16
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    4 Bedrooms / 5 Bathrooms / Sleeps 12
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    Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large living room and dining room with a kitchen that overlooks your own patio. Lush... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect 'get away' spot for individuals looking to fully immerse themselves in Key West culture. This house is... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island;... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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 neighborhood only 10 minutes to Duval Street and only 5-10 minutes to Smathers Beach. 3... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    ***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom 'home away from home' sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St,... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the... View all property information
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    Key West, Florida Keys 33040
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    6 Bedrooms / 6 Bathrooms / Sleeps 22
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    Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply... View all property information
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    Key West, Florida Keys 33040
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    11 Bedrooms / 9 Bathrooms / Sleeps 32
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    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE... View all property information
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    Key West, Florida Keys 33040
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will... View all property information
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    Key West, Florida Keys 33040
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    5 Bedrooms / 3 Bathrooms / Sleeps 18
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of... View all property information
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    Key West, Florida Keys
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    1 of 5 stars (1) Terrible
    1 Bedroom / 1 Bathroom / Sleeps 6
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    Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full... View all property information
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    Key West, Florida Keys 33040
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the island. Smuggler’s Den, a delightfully... View all property information
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    Key West, Florida Keys
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    This Historic home was built in 1895 and lovingly restored in 2001.This is one of only two eyebrow style homes in Key West that have a front dormer in the roof for architectural appeal. Although this home is an historic treasure, it is fully equipped with all modern conveniences including a heated... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 5 Bathrooms / Sleeps 6
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    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Downtown Key West, one block from Southernmost Point, one block from Hemingway House, walking distance to all mojor tourist attractions, restaurants, galleries, beaches. Three bedroom, two bath totally renovated, on site parking, rear patio. Central Air, granite counters, stainless appliances.... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    This is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. This unit is immaculate! Classic and beautiful nautical themed two bedroom, two and a half bath 3 story townhouse. Enter the home through your private gated tropical courtyard. The first floor open concept... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Two bedroom, two bath, totally renovated in 2015, all new, marble floors, 10 foot ceilings, granite counters, walking distance to all major tourist attractions, one site parking, one block from Southernmost Point, one block from famous Duval Street. local beach is less than one mile, restaurants,... View all property information
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    Key West, Florida Keys 33040
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. From the moment you step up onto the front porch, which is perfect for people watching, and into the open... View all property information
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    Key West, Florida Keys
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    4 Bedrooms / 3 Bathrooms / Sleeps 7
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    SOUTHARD LOVE Simply tell your friends and family to meet you at the corner of Southard Street and Love Lane, one of Key West’s premier Old Town addresses. This spectacular, three-story, historic and award-winning home has been fully renovated to meet the most discerning tastes. Dappled sunlight... View all property information
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    Key West, Florida Keys
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This charming conch home is uniquely located on a corner property across the street from The Studios of Key West, in the heart of the Old Town historic district. The Studios of Key West is the epicenter of Key West's cultural scene offering a dynamic mix of special event, community workshops,... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 5 Bathrooms / Sleeps 9
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    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West... View all property information
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    Key West, Florida Keys 33040
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    For adults only. You have use of one of four private cabins with a private marine style bathroom. You will share the common areas with new friends. The cabin is air conditioned with a queen like bed. Captain Charles and wife Deborah use one cabin. The space has a common living area with a sitting... View all property information
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    Key West, Florida Keys 33040