Home Vacation Rentals By Owner In Key West, FL

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$1891.88

/ Nightly
Private Vacation Home

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Key West, Florida, United States

Octopus’s Garden — Top-Rated Key West Rental with 150+ 5-Star Reviews!brbrLocation:brSteps from Duval Street & Ernest Hemingway’s Home, right in the heart of Old Town Key West.brbrThe Home:brA beautifully remodeled 3-bedroom, 3-bathroom historic home with a modern interior.brbrKey Features:brbrLiving Areas:brFormal parlor/sitting area with sofa sleeper, built-in hallway office, spacious living/dining room with oversized couches, 70 TV, and large wood dining table.brbrChef’s Kitchen:brCalacatta marble countertops, farmhouse sink, KitchenAid stainless steel appliances, pantry, and breakfast bar. Opens directly to pool deck—perfect for entertaining!brbrBedrooms:brbrMaster: King bed, sitting area, mini fridge, 65 curved TV, SONOS system, walk-in closet, pool access, oversized ensuite bath with his & hers vanities.brbrBedroom 2: King bed, large closet, 35 TV, SONOS speaker, ensuite bathroom with shower.brbrBedroom 3: Queen bed, armoire storage, 35 TV.brbrBonus Room: Foyer/den with queen pull-out couch and extra linens.brbrOutdoor Space:brLarge pool with water feature, travertine pavers, tropical landscaping, 6-foot privacy fence, outdoor shower, and a glowing 12’ custom metal octopus art piece.brbrParking:brOne assigned off-street parking space for a standard car or SUV.brbrExtras:brAbundant lighting inside/outside, washer/dryer, earplugs provided for possible noise from nearby nightlife.brbrSecurity:brSurveillance cameras at front door and side yards for added safety (no cameras in private areas).brbrConcierge Services:brPre-arrival grocery delivery, event planning, dining recommendations, and personalized local tips.brbrImportant Note:brbrDue to proximity to Duval Street nightlife, some noise may be heard. Earplugs are available in each bedroom.
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Exceptional(2)

Select Dates for Price
Condo

Poolside Palms - Truman Annex 2/2 Shipyard Condo

Key West, Florida, United States

If island living in a verdant park setting sounds appealing, this 2 bedroom, 2 bath condo fits the bill perfectly. Nestled in Truman Annex, Key West’s most exclusive gated waterfront community, this second-floor residence named Poolside Palms is centrally located for easy walking or biking to all there is to do and see. Plus it offers loads of amenities: reserved parking; a spacious balcony that lets you enjoy what locals call “the sweet weather”; and close access to a residences-only pool with lots of comfy lounge chairs. Yet impact doors and windows guarantee you absolute peace and quiet inside the residence. brbrLocated down a garden path past wooden structures reminiscent of 17th century New England architecture are double-story condos called The Shipyard. Poolside Palms is located on the second story which creates more privacy and better views. Behind a coded security lock and up a short flight of stairs, the first thing you notice is the striking abundance of natural light from windows and doors. The living, dining, and kitchen flow together in an open floor plan with high ceilings. The eye is immediately drawn to the French doors at the living room end that open onto a balcony with chairs, table for two, and an inviting lounge recliner. The balcony is so spacious it can be accessed from the Master bedroom as well. The tree-top view is of vibrant green palm trees swaying in a warm ocean breeze which begins to explain the condo’s apt name. From here you can even smell the refreshing crispness of salt water close by.brbrThe living room area provides what you need for comfortable seating whether you want to have a conversation, read your vacation book or magazine, or watch sports and movies on the large flatscreen TV conveniently located for viewing. Choose the large, comfy couch or one of the equally comfy chairs. A rattan and glass coffee table make it easy to imagine having beverages and snacks here. Under the TV is a rattan, white-washed wood cabinet with three drawers and two doors that is not only decorative but also great for storing stuff out of sight. Of course there’s central AC, cable, high-speed internet, DVD player, three flat-screen TVs, hardwood floors, and ceiling fans throughout. The whole residence is immaculate. brbrWhether you choose to dine alfresco on the balcony or inside, a dining table and four rattan chairs are located very conveniently between the living and kitchen areas. It’s the ideal spot to enjoy a morning pastry or lunch plate of leftovers warmed in the microwave from a meal out the night before. The galley kitchen is extremely ergonomic with key functions clustered near each other. Cabinets above and below store all the accoutrements you’d need to prepare a four-course meal or make a simple sandwich. The essential appliances are at your fingertips: refrigerator, stove, microwave, dishwasher, disposal, coffee maker, and more. And with cabinets above and below, there’s plenty of storage. Two artisan stools at the far end of the kitchen counter provide a perfect informal place for sitting, snacking, or sipping any kind of beverage you can think of. At the other end is a large window overlooking tropical landscaping and the inviting pool below that is for the exclusive use of Shipyard guests.brbrIn a closet just off the kitchen is Whirlpool’s latest style stacked washer/dryer in case you need to do a load or fluff some beach towels. To the right is the King bedroom where the bed can easily be separated into two twins if that configuration suits your needs. This bedroom has a generous window looking out at tropical foliage and down at the sparkling pool. But remember that the impact glass means full sight but no sound echoes. There’s a ceiling fan, a flatscreen TV perfectly located for viewing from the bed, bedside tables with lamps and drawers, and a closet with plenty of space for hanging items and folded items. The full bath is adjacent and perfectly laid out in terms of floor plan. The other bedroom, the queen bedroom that opens onto the balcony, offers similar amenities: very comfy bed, ceiling fan, flat screen TV, side tables, closet storage for hanging and for folded items, and a full ensuite bathroom. brbrWhen you’re ready to explore Key West, leave your car in its reserved space because world-famous Duval Street is only two blocks away. Stroll through the manicured landscaping, verdant palms, and interconnecting pathways that give this Truman Annex neighborhood its park-like atmosphere. Then head out through the wrought iron privacy gate to find yourself immersed in the sights and sounds of Duval’s attractions. brbrCheck out the tours, museums, shopping, and over four hundred restaurants/bars, many with open-air seating, some on the first floor, some on the second, and some right on the water. If you’re interested in watersports, there’s all kinds: diving, fishing, parasailing, snorkeling, and jet skiing to name a few. Don’t miss the Butterfly & Nature Conservatory at the Atlantic Ocean end of Duval and the nightly sunset celebration at Mallory Square on the Gulf of Mexico. Gather with other visitors and locals alike to applaud as the sun slips below the horizon. After sunset, stick around for the street party that follows. brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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Exceptional(2)

$2059.55

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Private Vacation Home

The Greenmoor House at Lunara Bay

Key West, Florida, United States

Summary:brbrDiscover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community! The Greenmoor House is a 6BR, 6.BA luxurious new build offering exceptional amenities, including: free gym access and ample living space perfect for relaxation and entertainment. With modern design and high-end finishes, this property is ideal for those seeking comfort and style. Experience a new level of living that combines elegance and convenience in this remarkable home.brbrbrbrThe Space:brbrExperience luxury with our private boat excursions and chauffeur services. Enjoy customized aquatic adventures or arrive in style with our premium transportation options. Expect excellence tailored to your stay. For more information, please reach out!brbrThe open-concept floor plan, both indoors and outdoors, creates a warm atmosphere ideal for entertaining and quality time with loved ones. Whether you're relaxing by the pool, playing games, grilling, or dining in various areas, there's something for everyone. The fully equipped kitchen is perfect for home-cooked meals or for a private chef to elevate your culinary experience. With high-speed internet and keyless entry, your vacation will be seamless and convenient. Outside, the spacious fenced yard provides a safe play area for children and a perfect space for your pets.brbrBed layout:brbrBedroom 1: King BedbrbrBedroom 2: Two bunk beds brbrBedroom 3: King BedbrbrBedroom 4: King BedbrbrBedroom 5: King BedbrbrBedroom 6: King BedbrbrAll bedrooms feature ensuite bathrooms.brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. brbrBoating & Private Dock Slip: We encourage boating. Here's what you need to know in order to do so safely: - Dock accommodates a boats up to 40’ in length. brbr- There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to Modern Keys, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Private washer/dryer - Located in a gated community - Free gym access at FYT - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.
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Exceptional(1)

$2519.19

/ Nightly
Private Vacation Home

The Fairhaven House at Solaire Lunara Bay

Key West, Florida, United States

Summary:brbrExplore the Fairhaven House, a new build at Lunara Bay - a collection of 26 luxury homes in a gated community! Featuring eight spacious bedrooms and a private pool. This stunning home offers top-tier amenities, including complimentary gym access and expansive living areas perfect for both relaxation and entertaining. Boasting a modern design and high-end finishes, this property is ideal for those seeking a perfect blend of comfort and style.brbrbrbrThe Space:brbrExperience luxury with our private boat excursions and chauffeur services. Enjoy customized aquatic adventures or arrive in style with premium transport options—all tailored to your stay.brbrThe open-concept design, both indoors and outdoors, creates a warm atmosphere for entertaining and spending quality time with loved ones. Relax by the pool, play games, grill, or dine in various areas—there’s something for everyone.brbrThe fully equipped kitchen is perfect for home-cooked meals or a private chef. With high-speed internet and keyless entry, your vacation is seamless. Outside, the fenced yard offers a safe space for children and pets.brbrbrbrBed Layout:brbrThis property features eight bedrooms, each with a king bed and ensuite bathroom.brbrbrbrDiscover a new standard of living where elegance meets convenience in an exceptional setting. Get ready to elevate your lifestyle in a space that truly feels like home!brbrbrbrGuest Access:brbrOur self check-in ensures a seamless arrival. Guests will receive a personalized access code before arrival, along with direct contact information for a local guest experience manager to assist with any questions, needs, or recommendations during their stay.brbrbrbrBoating & Private Dock Slip:brbrWe encourage boating! Here’s what you need to know for a safe experience:brbrThe dock accommodates boats up to 40 feet long.brbrThere is no power or pump-out service at the slips.brbrNavigating the Florida Keys can be challenging, so please proceed with caution.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for the day at Stock Rock Café, or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway—Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to Modern Keys. The driveway allows parking for up to four vehicles and a boat trailer. If you didn’t travel by water, you can also launch your boat at one of the public ramps in Key Haven or Stock Island. Rent a golf cart, scooter, or bike for the day to explore the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Extend your stay 7+ nights for 10% off your entire stay!brbr- Elevate your stay and ask us about our Private Chauffeur services.brbr- Private washer/dryer brbr- Located in a gated community brbr- Free gym access at FYT brbr- Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.
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Bath 8

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Sleep 16

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Exceptional(1)

$2029.5

/ Nightly
Private Vacation Home

The Joyrise House at Solaire Lunara Bay

Key West, Florida, United States

Summary:brbrDiscover a luxurious new build at the Joyrise House at Lunara Bay - a collection of 26 Luxury homes in a gated community! Featuring six spacious bedrooms and a private pool, this stunning home offers exceptional amenities, including: free gym access, boat docking for up to 40’, ample living space perfect for relaxation and entertainment and curated itineraries from our local guest experience team.brbrbrbrExtend your stay 7+ nights for 10% off your entire stay!brbrbrbrThe Space:brbrExperience luxury with our private boat excursions and chauffeur services. Enjoy customized aquatic adventures or arrive in style with our premium transportation options. Expect excellence tailored to your stay. For more information, please reach out!brbrThe open-concept floor plan, both indoors and outdoors, creates a warm atmosphere ideal for entertaining and quality time with loved ones. Whether you're relaxing by the pool, playing games, grilling, or dining in various areas, there's something for everyone. The fully equipped kitchen is perfect for home-cooked meals or for a private chef to elevate your culinary experience. With high-speed internet and keyless entry, your vacation will be seamless and convenient. Outside, the spacious fenced yard provides a safe play area for children and a perfect space for your pets.brbrBed layout:brbrBedroom 1: King BedbrbrBedroom 2: King BedbrbrBedroom 3: King BedbrbrBedroom 4: King BedbrbrBedroom 5: King BedbrbrBedroom 6: King BedbrbrAll bedrooms feature ensuite bathrooms.brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. brbrBoating & Private Dock Slip: We encourage boating. Here's what you need to know in order to do so safely: - Dock accommodates a boats up to 40’ in length. brbr- There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane - the driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Private washer/dryer brbr- Located in a gated community brbr- Free gym access at FYT brbr- Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximumbrbr- Elevate your visit with our Private Chauffeur Service for effortless transportation.brbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.
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Exceptional(2)

$294.65

/ Nightly
Private Vacation Home

SUN DAY, FUN DAY ~ Renovated 2/2 Home 2 Blocks from Beach in Casa Marina!

Key West, Florida, United States

WHIMSICAL ABODE TWO BLOCKS FROM THE BEACHES…brSteal away from the mainland to this equatorial slice of utopian delight! This classic mid-century modern home is set against the backdrop of the coveted and vibrant Casa Marina neighborhood. Sun-drenched days and sublime moments beckon you to this quiet south-end hideaway of famous downtown Duval Street, where fabulous galleries, fine dining and Key West attractions await you.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brFrom the gate, walk the short pathway to the welcoming double door entrance, where light-filled vaulted ceilings and terra cotta floors lure you into this home's cool embrace. Flow and functionality punctuate the open living and dining space, merging comfort and convenience for your enjoyment. Capture treasured time with loved ones in this chic and cozy gathering space as you rest on plush furnishings and sip on island-inspired cocktails. A large TV invites mindless and relaxing sessions (equipped with YoutTube TV) with your favorite movies or shows. The adjacent modern galley kitchen with refrigerator drawers, a countertop ice machine, full range and dishwasher are streamlined to maximize everything a chef requires for crafting memorable meals with all the culinary tools and appliances required. For your convenience, a full size washer/dryer and refrigerator/freezer reside in the garage. brbrSLEEPING ARRANGEMENTS…brJust off the living area, the primary king bedroom is an airy and soothing space enjoy a peaceful rest. Unclutter your weary mind as you sink down into soft bedding that cradles you into a peaceful slumber. Wash off the sun and sand in your ensuite bathroom with walk-in glass and tile shower and single vanity cabinet with storage. A private door to your personal sitting area in the garden is perfect for morning coffee. Step down to the adjacent guest room where your loved one will enjoy a plush king bed, ensuite bathroom with shower/tub combination and storage closets and clothing dresser. brbrOUTOOR LIVING… brSurrounded by verdant garden spaces, lush landscaping and spacious front and rear patios for relaxing or dining under sultry stars, you are enveloped in the exotic grounds and balmy island breezes that is the quintessential Key West lifestyle. A copper fire pit and chiminea create a cozy space.brbrPARKING... brThis home does not have a designated parking spot, however, parking is generally available on the street in front of the home.brbrPETS...brPets are considered at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night min). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrYOUR ISLAND PLAYGROUND AWAITS…
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Exceptional(1)

$315.32

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Private Vacation Home

Bohemian island home full of color and modern amenities - in a great location

Key West, Florida, United States

Welcome to Casa Del Sol, a colorful and effortless island stay! From the moment you step in the front door, you will take notice of the open-concept layout, bohemian furnishings, and lovely tropical theme. The living room's oversized sofa and large Smart TV offer the perfect combination for family hangouts. The adjacent full kitchen boasts a turquoise backsplash, stainless steel appliances, and granite countertops. After you whip up delicious dishes in this space, dine as a family around the wooden dining table. brbrEqually bright and beautiful, the home's bedrooms come adorned with high-quality linens, tasteful artwork, and TVs. Additional interior perks include a private washer/dryer, central air-conditioning, and a collection of board games. brbrOutside, enjoy the fresh sea breeze from the front porch or on the patio. Being nestled in a prime location, Key West's many amusements are at your fingertips! Get out and explore Hemingway Home and Museum, Key West Butterfly and Nature Conservatory, Smathers Beach, Florida Keys Eco-Discovery Center, and Fort Zachary Taylor Historic State Park. brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by the good neighborpolicy 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.
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