Home Vacation Rentals By Owner In Key West, FL

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Exceptional(8)

$561.45

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Private Vacation Home

Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining

Key West, Florida, United States

Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, gated community, this luxury two-bedroom retreat showcases tranquil tropical decor and comes well-appointed with all the modern essentials of home. Whether you're visiting with the kids or sneaking away for a romantic couple's escape, you're sure to find everything you need for carefree vacation comfort. Prepare anything from morning coffee to full family dinners in the well-equipped kitchen and dine together at the nearby table. The private deck comes furnished with a gas grill and outdoor dining table if you want to enjoy some fresh Florida breeze with your meal. You can also bust out your favorite board games or settle outside on the large front porch and get some fresh Florida air. Enjoy access to a heated outdoor pool - the ideal place to unwind after exciting days out. In the evenings, relax in the airy living area while streaming shows and movies on the smart TV.brTHINGS TO KNOW:brEnjoy central walkability with Southern Most Point, the Lighthouse, the Key West Butterfly and Nature Conservatory, and the Ernest Hemingway Home and Museum, all within blocks from home. Experience unforgettable live entertainment and explore local galleries, shops, bars, and restaurants along Duval Street, just a short walk from home. Additionally, Fort Zachary Taylor State Park is only a mile west, where you'll find historic sites, beaches, and walking trails.brThis property is managed by Seven Keys Vacations by Casago.
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Exceptional(16)

$274.95

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Apartment

Charming 2nd-story apartment with balcony & lighthouse view - walk everywhere

Key West, Florida, United States

Welcome to Julia Whitehead Lighthouse 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 was living 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, in the shadow of the lighthouse.brbrHere, in the upstairs Seagrass Suite, enjoy peaceful mornings with coffee on your private balcony, with a view of the Key West Lighthouse. Interior space combines modern updates with antique accent pieces, eclectic art, and cheerful pops of color. The modern, sleek kitchen makes meal prep a breeze and a cozy living room is designed for relaxing at the end of the day. Free WiFi and cable will keep you entertained, or unplug entirely with an evening back out on the balcony, enjoying the stars and the lights of Old Town before bed - another idyllic day in Key West awaits tomorrow.brbrThings to KnowbrA booklet inside the apartment features the full story of Julia Whitehead Guest Suites.
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Exceptional(8)

$487.06

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Private Vacation Home

Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi

Key West, Florida, United States

Enjoy modern Key West vibes with this home's bright accent colors, eye-catching tile work, and of course the sparkling private pools! Make no mistake, there are two heated saltwater pools that you're free to enjoy all throughout your stay, both surrounded by lush greenery. Rinse off in the outdoor shower if you're coming back from the beach! This single-level home is a duplex with two different sections, so the group can spread out and enjoy their own space or just enjoy double the amenities. Open up the wide glass sliding doors and enjoy seamless indoor/outdoor living with plenty of seating options (including poolside!).brbrBoth full kitchens are stocked with equipment so that you can cook up something delicious, and each flows perfectly with their living room and outdoor relaxation areas. Don't worry, there's enough dishes, glassware, and cutlery to help you enjoy those meals. Central air conditioning will keep everything mellow. Throughout the house, guests can rest in bright bedrooms with unique art and quilt-style bedding that definitely shows off the Key West spirit. The bathrooms feature tile work that's just as stunning as the kitchen's - each standalone shower features intricate tile work on the floor and wall. Selfie-friendly ambient light mirrors will help you start off the day with a sunny disposition. Luxury amenities pair up with bright, eye-catching details in this vacation home!brbrWhat's nearby:brIf you're looking to head straight to the beach, Higgs Beach is just half a mile away. The Southernmost Point of the continental United States is just over a half-mile away - take a picture and then enjoy some conch fritters at the Southernmost Beach Cafe. Take in a bit of history at the Ernest Hemingway Home and Museum just under one mile from the home. But if you're looking for a different kind of escape less than one mile away, take a walk through a sanctuary of colorful birds and over 50 species of butterflies at the Key West Butterfly & Nature Conservatory.brbrThings to know:brFour twin beds are pushed together to make two king-sized beds in the photosbrSnowbird-friendlybrLuggage dropoff allowedbrGuests must stay for a minimum of 28 nightsbrBeach towels are available for guest usebrStep-free access to common areabr*Island Retreat and Island Hideaway are smaller properties within Tropical Vibes, each with their own private pool. They can be rented separately or together.brThis property is managed by Seven Keys Vacations by Casago.
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Exceptional(6)

$190.26

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Private Vacation Home

Waterfront, Single-Story Home on a Canal w/ Dock, Kayaks, AC - 1 Small Dog OK

Key West, Florida, United States

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story home provides a canal-front dock where you can park your boat, two kayaks to take out each morning, and incredibly close proximity to open water two doors down. After a day spent boating and fishing, you can rinse off in the outdoor shower, toss the day's swimsuits in the washer/dryer, and cool of in the bright, tiled, and air-conditioned living space. There's a gas grill on the patio to sear your fresh catch for dinner, a fully appointed kitchen where you can prepare all the side dishes, and a lovely screened-in porch where you can dine al fresco, sip cocktails, and enjoy the glow of the sunset. Use the free WiFi to make plans for tomorrow's adventures, gather around the flatscreen TV in the living room for movie night, and sleep soundly in one of three bedrooms. The master suite features a king-size bed, sliding doors that open to the patio, and an en suite bathroom. The second bedroom has a queen-size bed and the third has two twin beds; the two rooms share the hallway bathroom.br brWhat's nearby:brThis canal-front home is located in a great neighborhood of Big Coppitt Key, with a number of eateries and conveniences a few blocks away on Overseas Highway. The heart of historic Key West is an easy, nine-mile drive west, where you'll find such legendary attractions as the Key West Historic Seaport, the Ernest Hemingway Home and Museum, Southernmost Point, Mallory Square, and the lively shops, restaurants, and bars that line Duval Street.brbrThings to know:brFull kitchenbrOne small dog is welcome for a nightly feebrConstruction equipment/vehicles are prohibited from being parked on sitebrNo smoking and no parties, pleasebrThere is a 28-night minimum stay for this propertybrbrThis property is managed by Seven Keys Vacations by Casago.
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Exceptional(10)

$171.68

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Private Vacation Home

Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything

Key West, Florida, United States

*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.*brbrIf Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island!brbrYou'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well as all the well-known sites, including famous Duval Street. Take a stroll to Ernest Hemingway House and Museum then head to Southernmost Point Beach for an afternoon of lounging on the sand, soothed by the sound of the crashing waves. Fort Zachary Taylor Historic State Park and the National Marine Sanctuary are a mile to the west, and Mallory Square, which offers more shopping and dining, is a mile to the north. The family dog is also welcome to join you here for an additional nightly fee.brbrAfter a fun day of exploring, head home to your tastefully decorated getaway to freshen up, then treat yourself to a mouthwatering seafood dinner at The Little Pearl. Or stay in and work your magic in the full kitchen and enjoy your feast at the small dining table or relax in the living room and watch some a cable show or movie on the flatscreen. The free WiFi will help you get around and create your ideal itinerary, and the private washer and dryer will keep your clothes and humble abode sand free.brbrBook this adorable home today, and get ready for your rejuvenating Key West getaway!brbrThis property is managed by Seven Keys Vacations by Casago.
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Sleep 4

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Exceptional(127)

$387.53

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Condo

Resort suite with pool, hot tub, tennis & full kitchen

Key West, Florida, United States

Exquisite 2-bedroom condo that has been extensively updated and completely remodeled, featuring beautiful new vinyl plank flooring, stainless steel appliances, granite countertops, and fully renovated bathrooms, along with many additional upgrades. New photos coming soon!brbrMake those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from start to finish. One dog is allowed.brbrThis rental is part of the exclusive Sunrise Suites Resort, conveniently located only a short drive from the Key West International Airport on the east side of the island. With a covered parking spot, bicycle rentals, it's easy to reach Key West's most popular attractions in just a few minutes! Stroll along the historic boardwalk, try to spot Cuba from the Southernmost Point, or go snorkeling through the island's colorful coral reefs.brbrIf you'd rather stay closer to home, you'll find plenty at the resort to keep you entertained. Take a nap in the shade of a palm tree beside the lagoon-shaped pool, sink into the bubbling waters of the community hot tub, or get your heart rate going in the fitness room. Upstairs, you'll find cable, free WiFi, and a fully equipped kitchen for your use, along with a private balcony for relaxing on. With tropical landscaping at every turn, you'll never be far from Key West's beautiful scenery.brbrYour next favorite vacation is waiting! Book your reservation today.brbrTHINGS TO KNOW
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Exceptional(1)

$230.47

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Condo

Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views

Key West, Florida, United States

Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large balcony overlooking the Gulf, and take in one of the breathtaking sunsets Key West is known for.brbrTarpon Watch is part of Sunset Marina Residences, a gated Gulf-front community on Stock Island, also known as 'the new Key West.' On the grounds, you'll have access to a waterfront pool and hot tub, a long meandering dock for wildlife-watching, and a dedicated parking space in a covered garage (along with ample visitor parking). For boating or fishing, feel free to inquire for details about boat rentals/slips. Or, simply drive or hop in an Uber to Old Town or Smathers Beach.brbrNewly and beautifully renovated throughout, this first-floor condo is full of bold colors, comfortable furnishings, and elegant finishes. There are thoughtful touches at every turn, including a well-equipped kitchen with stainless steel appliances, a wet bar with a wine fridge for evening cocktails, and TVs in the living room and both bedrooms. Each bedroom is paired with its own bathroom, including a primary suite with a walk-in closet, both a shower and a jetted tub, and direct access to the balcony.brbrBonus features of the condo include a sleeper sofa in the living room, a private washer/dryer to help you pack light, and central air conditioning and heating to keep you comfortable all year round.brbrThings to Know:brStreaming services are available with guests' own account credentials.brCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll 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 AM.brNo smoking is permitted anywhere on the premises.brThis property is managed by Seven Keys Vacations by Casago.
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$241.45

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Private Vacation Home

Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach

Key West, Florida, United States

Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West.brbrThis home lies just two blocks away from Higgs Beach and the Edward B Knight Pier, putting you in a prime location to enjoy one of Key West's best stretches of surf and sand. You'll also be just over a mile from many of Key West's most popular attractions, including the Southernmost Point, the Ernest Hemingway House, and the island's many bars and restaurants.brbrBack home, escape the crowds with a relaxing soak in your private pool, then mix yourself a tropical cocktail and stretch out in the hammock for a lazy afternoon nap. When you get hungry, wander inside to fix dinner in the fully equipped kitchen, then enjoy your meal out on the deck or in front of the flatscreen TV. Free WiFi, central A/C, and a private washer/dryer are also provided for your convenience.brbrThere's no better way to experience Key West than a stay at this first-class home. Book today!brbrThings To Know:brThis property is managed by Vacasa Florida LLC.brPlease 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.
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Sleep 7

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Exceptional(124)

$391.53

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Condo

Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

Key West, Florida, United States

Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom condo is part of the upscale Sunrise Suites Resort, where tropical comfort meets resort-style amenities.brbrStep onto your private deck to soak in the island breeze, then spend your day swimming in the heated pool, unwinding in the hot tub, or hitting the on-site tennis courts and fitness center. With marinas, beaches, Old Town shops, and Key West's lively dining scene just minutes away, every day can be as relaxing—or adventurous—as you choose.brbrInside, Sunset Suite -- Catalina Suite 311 offers all the comforts of home, including central AC, free WiFi, cable TV, and a fully equipped kitchen. Two spacious bedrooms ensure restful nights, while on-site parking and elevator access make getting around a breeze. Even better, your pup can join the fun—this condo is dog-friendly for a small nightly fee.brbr✨ Highlights of Sunset Suite -- Catalina Suite 311br • ️ 2 bedrooms for comfort and privacybr • Private deck with tropical viewsbr • Resort pool & hot tubbr • Tennis courts + fitness centerbr • Dog-friendly (small fee)br • Free WiFi + cable TVbr • Fully equipped kitchen with modern appliancesbr • On-site parking + elevator accessbr • ✈️ Minutes to Old Town, marinas, and the airportbrbr Points of Interest Nearbybr • Smathers Beach – 1.5 milesbr • Higgs Beach – 2.5 milesbr • Southernmost Point – 3.5 milesbr • Duval Street / Old Town Key West – 3.5 milesbr • Mallory Square Sunset Celebration – 4 milesbr • Key West Butterfly & Nature Conservatory – 3 milesbr • Ernest Hemingway Home & Museum – 3.5 milesbr • Fort Zachary Taylor Historic State Park & Beach – 4 milesbr • Key West Golf Club – 3 milesbrbr ️ Shopping & Diningbr • Publix Super Market – 1.5 milesbr • Winn-Dixie Grocery – 2 milesbr • Local Boutiques & Galleries – Along Duval Street (3.5 miles)br • Key West Farmers Market (Thursdays) – 1.5 milesbr • Popular Restaurants Nearby:br • Hogfish Bar & Grill – 2 milesbr • El Siboney (authentic Cuban) – 3 milesbr • Conch Republic Seafood Co. – 4 milesbrbr Your Key West Escape AwaitsbrbrWhether you're here for laid-back beach days, world-class fishing, or the nightlife of Old Town, Sunrise Suites – Catalina Suite 311 is the perfect home base for your Key West adventure.brbr Book your stay today and experience the island lifestyle in comfort and style!brbrTHINGS TO KNOWbrUnit offers a shared, paid laundry room on site
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Exceptional(7)

$1101.38

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Private Vacation Home

Historic Old Town home with three apartments, balcony, & lighthouse view

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 was living 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 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, in the shadow of the lighthouse.brbrMade up of three individual one-bedroom apartments, the suites are the perfect choice for several couples or families traveling together. Each of the three features a full, modern kitchen, AC splits, TV, and free WiFi. brbrAt charming Coral Cove, you'll find an updated, modern space with colorful, beachy decor and a cozy bistro table on your enclosed patio. In the upstairs Seagrass Suite, enjoy peaceful mornings with coffee on your private balcony, with a view of the Key West Lighthouse. Interior space combines modern updates with antique accent pieces, eclectic art, and cheerful pops of color. brbrFinally, at Mermaid's Retreat, you'll find a beautifully updated space, with colorful, eclectic decor and abundant natural light. Balconies off both the living room and bedroom upstairs are ideal for languid afternoons with a good book and some sweet tea. When bedtime calls, three serene sanctuaries offer a restful night's sleep. It's time to make that Key West getaway a reality at Julia Whitehead Guest Suites - all that's left to do is book. brbrTHINGS TO KNOWbrA booklet inside the apartment features the full story of Julia Whitehead Guest Suites. brThere is no parking available at this property.
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Exceptional(11)

$216.11

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Private Vacation Home

Old Town Key West classic with private saltwater pool & enclosed patio- by shops

Key West, Florida, United States

This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the patio table and chairs, lounge, gas BBQ grill, outdoor shower, pool floats, and heated saltwater pool accented with underwater lighting. This beautiful home has everything you need to make your next Key West vacation memorable. You won't want to leave, and you will definitely want to come back.brbrThis classic Key West home is centrally located in Old Town, not far from the Southernmost Point of the United States. Numerous restaurants, sandwich shops, and a local grocery store are just a few blocks away. While in the area, stay active playing pickleball and tennis at the nearby courts as well as some classic shuffleboard. Tour the world-famous Duval Street, known for shopping, dining, and entertainment. Enjoy the beautiful sunsets at Mallory Square or dine at one of the many restaurants along the waterfront in the Historic Seaport District. Be sure to visit the nearby Key West's Butterfly Museum and Nature Conservatory, easily one of the area's best attractions.brbrTHINGS TO KNOWbrThe king bed may be separated into two twins upon request.brThis property is managed by Seven Keys Vacations by Casago.brNon-Reserved Street Parking Only. The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only,” and visitors are NOT permitted to park in them.
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