Vacation Rentals By Owner In Key West, FL

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(27)

$291.57

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.

Apartment

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

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$176.65

Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental features a spacious floor plan with doors that open out to the back patio to create an indoor/outdoor living space. Kick back in the living area and watch your favorite TV show or gather with your group and plan your next adventures. Bring the snacks made in the well-equipped, full kitchen outside and enjoy the breeze as you kick back in the outdoor dining area. Then take a dip in the shared swimming pool.brbrWHAT'S NEARBYbrSteps from Duval St. and a variety of entertainment, dining, and shopping options, you won't get bored here! Easily walk or bike to attractions such as Hemingway House, Key West Lighthouse, Harry Truman Little White House, Southernmost Buoy, Key West Butterfly and Nature Conservatory, and much more.brbrTHINGS TO KNOWbrShared laundry facilities on-site.brBeach/pool towels provided for guest use.brSnowbird-friendly. Please contact us for details.brPlease note that the pool, pool deck, and gas grill are occasionally shared with the owners when they visit.brThis home has a 28-night minimum stay per city regulations.brThis property is managed by Seven Keys Vacations by Casago.

Ground-level getaway with free WiFi, private deck, & shared outdoor pool

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(5)

$624.79

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*brbrHead to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. Dogs are also welcome.brbrThis rental is located in the heart of Old Town, putting you one short block from Duval Street and its well-known nightlife, and within walking distance to dining, shops, galleries, and beaches. The famed Ernest Hemingway Home and Museum is just around the corner, and Fort Zachary Taylor State Park is only a mile away.brbrWrap yourself in both style and comfort with this well-appointed home, which offers amenities like free WiFi, cable TV, central A/C, off-street parking, and a private washer/dryer. A dog is welcome. And with the pool just outside, you can satisfy your desire for a refreshing dip anytime you like.brbrBook this lovely home today, and come live the Key West lifestyle!brbr*Please note the 30lb. weight limit for dogs*brbr*Please note that last-minute bookings cannot be made online.brThis property is managed by Seven Keys Vacations by Casago.

Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$173.11

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(70)

$203.0

Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more!brbrPerfectly located between Truman Annex and Bahama Village, this comfortable condo sits only two blocks from the fantastic restaurants, nightlife, and shopping on Duval Street. Park your car in the off-street space, walk a quarter-mile to the Ernest Hemingway Home and Museum, and take afternoon bike rides to the soft sand at Fort Zachary Taylor Historic State Park three-quarters of a mile west.brbrThe living space has been meticulously decorated by one of Key West's preeminent designers, offering travertine floors, central A/C, free WiFi, and French doors that open to the deck. When you're not dining at Blue Heaven nearby, you can sip cocktails outside among the palms and orchids, flip through the cable offerings on the HDTV, and splash around in the shared swimming pool. A full kitchen with granite countertops, a private off-street parking spot, and a private washer/dryer are also on hand.brbrLet your Key West escape begin today - don't wait another minute to book this elegant condo!brbr*Please note that last-minute bookings cannot be made online. Contact us for details.*

Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(100)

$1087.32

Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love brbrLocated half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size!brbrFuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome. brbrPut life on hold for a moment and settle into paradise with these two cottages on Key West - book today!

Cabin

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(127)

$484.3

Bask in the tropics of Key West at this inviting cottage with a private heated pool and a lush backyard garden.brbrThis lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square.brbrStay cool with air conditioning, cook up food on the gas grill, and dine outside on pleasant evenings. Feel free to pack light, since a private washer/dryer lets you take care of any laundry. This home offers street parking in addition to the private parking area that will hold up to two compact vehicles or one full-size vehicle. brbrEnsure your vacation in Key West is comfortable and relaxing - book this cottage today! brbrThis property is managed by Seven Keys Vacations by Casago.

Cabin

Comfortable Cottage with Private Pool & Lovely Garden - Great Location

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(201)

$685.81

This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically landscaped back yard and a private, outdoor hot tub. This home also comes with convenient off-street parking for your vehicle.brbrWalk the streets of this adorable neighborhood that author Ernest Hemingway once called home and be sure to visit his former residence and museum located right around the corner. This part of Key West is packed with a number of other historical sights, homes, and museums including the Truman Little White House (less than a mile away) and the USCGC Ingham Maritime Museum, docked just a half mile from your front door.brbrBack home, enjoy the free WiFi and watch your favorite shows and movies on the four cable TVs. Out back, you can enjoy meals on the furnished patio or soak away your cares in your private hot tub. The front porch of this home also offers seating and a swing where you can close out your days and watch the sun set over Key West.brbrStart making plans for your next Florida vacation with the family or a few friends and book this classic, adorable home today. This property is managed by Seven Keys Vacations by Casago.

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(200)

$1041.19

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(87)

$326.25

Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and offers a full kitchen, living room, private bedroom, bathroom and sleeper sofa. Private deck just off the master bedroom. Large flat screen tv in living room. Located in the back of the property overlooking a shared common pool area. Large gas grill on property and washer-dryer .Off street parking spot. Enjoy your stay in a true conch home! Note: The property is set up for no contact check-in. The unit has been cleaned and sanitized by a professional cleaning company prior to your arrival. Cottage has many repeat renters so reserve as soon as possible.

Cottage

Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(134)

$423.23

Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by day and relax peacefully at night.brbrLocated on the eastern side of Key West, this condo is part of the exclusive Sunrise Suites Resort. When you're ready to explore, your rental is just a short drive to many of the island's most popular attractions. Scuba dive through crystal-clear waters, book a deep-sea fishing trip, or explore Key West's bustling shops and boardwalk. When you're ready for a break, you're never far from home, where you can rest up and refresh for another day of adventure!brbrCool off with a dip in the shared pool, enjoy a leisurely walk around the lush tropical grounds, or get your pulse up with a game of tennis. Cable and free WiFi are both provided, along with comfortable furnishings and a private balcony for taking the air. The family dog is also welcome to join you for an additional nightly fee.brbrTreat yourself to an incredible Key West getaway with this wonderful condo. Book your reservation today!brbrTHINGS TO KNOW

Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking

Key West, Florida, United States

Bed

Bath

Sleeps

$369.98

Playful pops of color, resort amenities, and a prime location await you at this marvelous vacation home! Whether you're out enjoying the sand and waves, taking a refreshing splash in a shimmering pool, or enjoying the charming comforts of your getaway, there is nothing short of possibilities and wonder here!brbrUpon entering, you'll be met with an inviting and serene space. There is a cozy living area with comfortable furnishings and a TV. Indulge in culinary delights in a full kitchen with stainless steel appliances and everything you need to whip up your favorite recipes. Come mealtime, you have the option of dining inside or out on the screened porch. Enjoy the fresh breeze on the deck before retreating to one of the comfortable sleeping spaces - another amazing day awaits tomorrow.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.

Colorful home in private community with resort pool & hot tub, on-site golf

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(101)

$443.2

Ideal for a small group or two couples traveling together and looking for a private, amenity-rich experience, this cozy second-floor tropical studio offers a well-equipped kitchenette, a furnished deck, and access to a swimming pool at the heart of a beautifully maintained tropical courtyard.brbrLocated two blocks from the southernmost beach and one block from Duval Street, the hottest street in Key West, restaurants, coffee shops, and fun nightspots are all a short stroll away. Duval Street also hosts a number of year-round special events, festivals, and parades, so be sure to check the community calendar once you arrive (or ask one of the friendly locals). Don't miss the Key West Butterfly and Nature Conservatory, less than a quarter-mile away, and be sure to visit the Ernest Hemingway Home and Museum to see how Papa lived back in the 1930s.brbrAt home, get online with ease thanks to the high-speed WiFi and keep up with all your favorite shows on the cable TV. Relax with a refreshing drink on your deck as the sun sets over Key West, or cool off in the swimming pool as the ocean breezes play through the palm trees above.brbrThings to KnowbrLast-minute bookings cannot be made online.

Apartment

Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach

Key West, Florida, United States

Bed

Bath

Sleeps

$172.02

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(144)

$351.64

Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed.brbrLocated on the eastern side of the island, this condo is part of the luxurious Sunrise Suites Resort. Wake up every morning surrounded by palm trees and beautiful landscaping, and get the blood pumping with a dip in the pool or an invigorating early-morning game of tennis. Afterwards, sip a cup of coffee out on the balcony and plan your day using the free WiFi.brbrYou'll have your pick of exciting activities, from scuba diving through the reef to relaxing on the sands at Smathers Beach, to kayaking along the stunning shoreline. A covered parking spot is provided for your convenience, along with bicycle rentals , making it easy to move from one location to the next. You'll also have a private washer/dryer.brbrWith Key West's most popular attractions less than five miles away, you're never more than a few minutes from an exhilarating tropical adventure. Book your reservation for this delightful condo today!brbrTHINGS TO KNOW

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(123)

$334.64

Escape to the sunshine and soft sands of the Florida Keys with this amazing home in Sunrise Suites Resort in Key West with a shared pool. Sporting updates such as brand-new appliances, new sound-proof flooring, and a stackable washer/dryer, your stay is guaranteed to be a comfortable one.brbrBack at home, you can stroll down a wooden walkway past a pristine pond, enjoy the shared hot tub or take a dip in the shared swimming pool. When you've toweled off, head inside to whip up a delicious meal in the kitchen, or simply kick back and relax with some cable on the TV. Stroll out to your private balcony and indulge in watching the birds at the Salt Ponds Preserve.brbrGet your next vacation started now - place your reservation today!brbrSHARED AMENITIESbr-Poolbr-Hot tubbr-Fitness roombr-Tennis courtbrbrTHINGS TO KNOW

Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room

Key West, Florida, United States

Bed

Bath

Sleeps

$360.8

Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and luxury king bed in the guest bedroom. Two living room sofas adds extra sitting. Nicely decorated with a Key West Flair. Full kitchen with all appliances, washer/dryer, electric range and microwave. Central air conditioning with ceiling fans. Flat screen TV and Wireless Internet provided. Large pool with hot tub and sauna. Lighted tennis court. Gated community with BBQ area. Dedicated, covered parking spot. brbrNote: The property is set up for no contact check-in. Two inflatable twin size blow up mattress are provided for additional guest over four. Max allowed is six guests.

Direct Ocean View from Your Condo-No Contact Check-In

Key West, Florida, United States

Bed

Bath

Sleeps

Exceptional(26)

$242.67