Home Vacation Rentals By Owner In Key West, FL

Showing 1480 Of 2059 Vacation Rentals
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Exceptional(1)

$179.6

/ Nightly
Condo

Dog-friendly condo near beach with pool, grill, outdoor shower, W/D, AC

Key West, Florida, United States

In the heart of Old Town and just two steps up to enter, this charming single-story cottage is the perfect setting for your next getaway with family or friends. This snowbird-friendly condo boasts an unbeatable location within walking distance of lively Duval Street, fantastic local restaurants, Higgs Beach (with volleyball and tennis courts), a drug store, gym, and neighborhood grocery store.brbrStep inside this centrally air-conditioned retreat and you'll be welcomed by a bright, airy floor plan featuring half-vaulted ceilings, exposed wood beams, and cheerful beach-inspired décor. Enjoy relaxing evenings with free WiFi, cable TV, or streaming on the smart TVs using your own accounts. A variety of puzzles and board games —Dominos, cards, Uno, Backgammon, Scrabble, Monopoly and more—offer plenty of entertainment options.brbrWhen it's time to dine, the spacious, well-appointed kitchen makes cooking a pleasure. It features all-new stainless steel appliances, including an induction cooktop with air fryer oven and a convenient beverage fridge. Additional highlights include a newly renovated bathroom, an in-unit washer and dryer, and complimentary off-street parking for one vehicle.brbrOutdoors, the property truly shines. The expansive shared common area is surrounded by magnificent palm trees and includes a heated outdoor pool, poolside loungers, and an outdoor dining space—perfect for soaking up the Key West sunshine. You'll also enjoy a private enclosed patio complete with a gas grill and a beautiful teak outdoor shower.brbrWith a 28-night minimum stay, this home invites you to truly settle in and experience the vibrant charm and laid-back beauty of picturesque Key West.brbrThings to KnowbrPermit number: 25230-138528brbrYou must be 25 years or older to rent this property.
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Exceptional(27)

$291.57

/ Nightly
Apartment

Charming, updated home near Duval St. with enclosed patio & walkable location

Key West, Florida, United States

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway lived a few houses down, it was home to a popular Cuban bodega. From the 1980s through the turn of this century, potter Charles Pearson created ceramic masterpieces which are still collected today. If you keep a watchful eye, you will find some of his ceramic fish adorning buildings and homes in the neighborhood still.brbrIts current guardians have spent nearly a decade painstakingly bringing the building back to life, with three one-bedroom apartments, and hosting Dog Tired Studio gallery up front as the proud face of the building. Julia Whitehead, the patron mermaid of the building, has been keeping an eye over this landmark since she first surfaced here in the 1800s, and she invites you to come and live like a local, just steps from Duval St., in the shadow of the lighthouse.brbrHere, at charming Coral Cove, you'll find an updated, modern space with colorful, beachy decor. The full kitchen makes it easy to whip up meals or snacks, and you can dine alfresco at the bistro table on your enclosed patio. Spend the day snorkeling at Dry Tortugas National Park, then let the AC splits in each room cool you down. Watch a bit of TV or use the free WiFi to scroll social media, then call it a night in the serene bedroom, with sweet dreams of mermaids and swaying palms in store.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighborpolicy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brA booklet inside the apartment features the full story of Julia Whitehead Guest Suites.
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Exceptional(6)

$173.11

/ Nightly
Private Vacation Home

Pool, Pet-friendly, Bicycles and 5 min walk to Beach

Key West, Florida, United States

Please note: This home requires a minimum stay of 28 nights or longer, as enforced by the HOA. No exceptions can be made.brbrWelcome to Conched Out Cottage, your ideal long-term island escape in the heart of Old Town Key West. This charming, dog-friendly monthly rental is perfect for small families, couples, or close friends looking to settle into the relaxed rhythm of island life—just minutes from the beach and the best of Key West.brbrSet in a quiet residential neighborhood just down the street from Higgs Beach, this inviting retreat offers the perfect balance of tranquility and convenience. You're close to Duval Street's lively restaurants, bars, and boutiques, as well as endless opportunities for outdoor island adventures. Spend sunny afternoons lounging by the heated shared pool (shared with only three other units), or explore the historic streets on the provided adult bikes.brbrInside, you'll find a bright, welcoming living space with comfortable seating, a flat-screen TV with cable, and free high-speed WiFi—ideal for both relaxing evenings and remote work. The fully equipped kitchen makes it easy to prepare home-cooked meals, while the private backyard patio with outdoor seating is the perfect spot for morning coffee, afternoon reading, or sunset cocktails.brbrThoughtful conveniences include a private washer and dryer, central air conditioning, and off-street private parking. Up to two well-behaved dogs are welcome with a small nightly fee, so your furry companions can enjoy island living too.brbrWhether you're planning a snowbird stay, a remote-work-friendly getaway, or simply a relaxing monthly rental in paradise, Conched Out Cottage offers a comfortable, charming home base to truly experience the Key West lifestyle.brbrBook your extended tropical stay today!brbrPlease note: last-minute bookings cannot be made online. Please call us for additional details.brbrThis property is managed by Vacasa Florida LLC.
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Exceptional(200)

$1041.19

/ Nightly
Private Vacation Home

Charming dog-friendly home with guest cottage & private pool - great location

Key West, Florida, United States

Slip into island time at Bahama House, a relaxed and inviting 3-bedroom, 3-bath retreat tucked away in the heart of Old Town Key West. Warm, welcoming, and full of tropical charm, this home is perfect for families and groups who want easy access to the fun of Duval Street while enjoying a peaceful, private oasis to unwind.brbr Space to Spread Out + Relax TogetherbrThe property features a cozy main house with two comfortable bedrooms and two full bathrooms, plus a separate private guest cottage with its own bedroom, bathroom, and kitchenette—perfect for grandparents, teens, or couples looking for a little extra privacy. Each space includes individual A/C units and ceiling fans so everyone stays comfortable.brbr Your Own Backyard Island ParadisebrKick back in a lush, palm-filled courtyard designed for slow mornings and long, sunny afternoons. Float in the heated private pool, read a book on the shaded patio, or fire up the grill for a family cook-out. The fully fenced yard creates a safe and private space for kids to play and for adults to unwind.brbr Comforts That Feel Like HomebrInside, the home is styled with relaxed island décor and includes a fully equipped kitchen with stainless steel appliances, fast Wi-Fi, smart TVs with streaming, and a comfy living room with a queen sleeper sofa for extra guests. A private washer and dryer make longer stays easy and breezy.brbr Bring the Whole Crew—Pups IncludedbrDogs up to 35 lbs. are welcome (with a pet fee), and beach towels, off-street parking, and accessibility-friendly features help keep your trip stress-free and simple.brbr Walkable Fun for EveryonebrStep outside and explore the best of Key West—cafés, shops, music, and attractions like the Hemingway Home & Museum are just moments away. Beaches and water activities, from snorkeling to sunset cruises, are only four blocks away.brbr☀ Live slow. Laugh often. Soak up the sunshine.brBahama House is where families come to relax, reconnect, and enjoy the island life—together.brbrBook your getaway today.brbrThings to KnowbrEnjoy complimentary pool heating set at a cozy 90°F! .brGuests are welcome to access available streaming services using their personal login credentials. brThis property is managed by Seven Keys Vacations by Casago.
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Bath 3

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Sleep 8

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$172.02

/ Nightly
Condo

Charming island retreat with balcony, king bed, desk space & dog-friendly vibe

Key West, Florida, United States

Welcome to Periwinkle Place—a bright, dog-friendly escape in the vibrant heart of Old Town Key West! Just one block from famous Duval Street, this charming two-level home offers the perfect blend of island relaxation and city excitement. From your front door, walk to top attractions like the Ernest Hemingway Home & Museum, Key West Lighthouse, Southernmost Point, and the crystal-clear waters of South Beach.brbrDesigned for both comfort and style, Periwinkle Place is ideal for couples, solo travelers, or small families—with room for one well-behaved pup up to 50 lbs. The upstairs bedroom features a luxurious king-size bed beneath vaulted ceilings, while the downstairs living area includes a comfortable double sleeper sofa to accommodate extra guests. A fully equipped kitchen and dining nook provide everything you need to enjoy meals at home.brbrFor those working remotely, you'll love the spacious desk area just off the bedroom—a perfect, quiet spot with plenty of elbow room and natural light to keep you focused and productive between island adventures.brbrEnjoy your morning coffee or evening cocktail from your semi-private balcony as you take in the lively energy of Old Town. Whether you're here for relaxation, discovery, or a little of both, Periwinkle Place offers a stylish and convenient home base for your unforgettable Key West escape.brbrTHINGS TO REMEMBER
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