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Key West Vacation Rentals

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 20
    4.5 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 23
    4.5 of 5 bubbles (42) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 21
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 bubbles (4) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    10% OFF already discounted prices for Open dates in April & May! Please call our office for details. Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please email Marie, the owner, for any inquiries. I'll be sure to promptly answer your emails and provide my phone number then. Thank you! The completely renovated Shabby Chicken - come stay with the large and proud newest bird in town!! 5-STAR rating and the best floor plan around. This ground... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 22
    5 of 5 bubbles (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (51) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    NEW UNIT! Reduced Introductory Pricing for 2017! Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
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    About this property
    Pineapple Cottage is a two bedroom, two bathroom home with a private pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (one block from Duval Street). Behind an enclosed, white wooden gate there is tropical... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4 of 5 bubbles (4) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Porch
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • Hot Tub
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor unit "Treetop" sleeps up to 2... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 11
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
    • Parking
    • Terrace
    • Air Conditioning
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    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Petite Maison is a designer Key West Guest Cottage that is located in the Gallery District of Duval Street. It is located on a quiet hidden lane behind Duval Street. Petit Maison is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which make it a perfect spot to... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (20) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (7) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Balcony
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This home has a unique pricing structure. While it can rent less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial Monthly Rental discounts. In addition, save 3% off published rates if you pay by check. Your space. Your vacation lifestyle. The Quilted... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (14) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Patio
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    3.5 of 5 bubbles (9) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    "In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern condominium, constructed within an important piece of historic American architecture. Situated along the gateway waterfront to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This END-UNIT with extra sunlight, ground floor condo is very clean, well-appointed and has beautiful linens, art work and comfortable beds. The Rooster Retreat along with my attention to detail and welcoming our guest has earned 35 5-STAR ratings (Listed with another vacation site). Come stay... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    About this property
    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! The Foundry is a non-smoking community within the Truman Annex. Classic and beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    OVERVIEW: Monthly Only. Right in Key West -- NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 7
    5 of 5 bubbles (32) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Sauna
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Scroll down to "About the owner" and in that box click on the "See more" button -... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    • Secure Parking
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Key West condominium, Casa Tropico is a 2 bedroom, 1 bath ground floor condominium. The master bedroom has a queen size bed, the second bedroom has 2 twins. A double set of French doors in the living room open onto the rear deck. The deck overlooks a quiet walking lane. Outfitted with table,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Satellite TV
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+   Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • DVD Player
    • Sauna
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool...
    • Washer
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    28 Night Minimum - Monthly Rentals Only 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. The front porch is perfect for people watching and chatting with locals... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (46) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    3 of 5 bubbles (1) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Balcony
    • Parking
    • Terrace
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 furniture including the sleeper sofa. The first floor features open and airy... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    THE BESS SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Recently... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (15) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    NEWS BULLETIN. JUST HAD A CANCELLATION FOR THE WEEK OF MAY 13 TO 20 SO I WILL DO RIGHT BY YOU WITH THE RATE. Now onto my cottage. . Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Patio
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
    Location Information
    Key West, Florida Keys 33040
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