Vacation Home Rentals By Owner In Key West, FL

brOur vacation rental, Island Time Escape, offers the perfect blend of comfort and convenience, providing you with a home away from home in this idyllic destination. Located just minutes from popular attractions like Duval Street, the Ernest Hemingway Home and Museum, and Mallory Square, you'll have easy access to everything Key West has to offer.brbrUnwind in our beautifully appointed accommodations, complete with modern amenities and charming island decor. Enjoy your morning coffee on a private outdoor deck, take a dip in the pool, or fire up the grill for a delightful evening barbecue. With its warm hospitality and inviting ambiance, our rental is the perfect place to create unforgettable memories.brbrThe main house consists of 2 bedrooms, 2 full baths, a large open kitchen and dining room. Both bedrooms and the living room open up to a beautiful pool, deck and landscaping. Additionally, there is a separate pool cabana perfect for an office including a murphy bed, half bath and outdoor shower for guests. brbrExperience the magic of Key West and discover why it's a favorite destination for travelers from around the world. We look forward to welcoming you to your tropical retreat! br

Island living 3-bed oasis w large pool, lush deck, cabana, outdoor shower

Key West, Florida, United States

Bed

Bath

Sleeps

$250.29

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis unit is a 30 night minimum. This is a 2 story unit.brBedrooms: 2brBathrooms: 2.5brLocation: Front StbrSquare Feet: 1220brParking: One assigned parking space in lotbrAmenities: Shared heated pool, TVs, Wifi, walkable to shops & restaurants downtownbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No commercial vehicles permitted in the parking lot.brPet Policy: One pet under 25 lbs. allowed with approval prior to booking and a non-refundable pet fee.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool

Key West, Florida, United States

Bed

Bath

4

Sleeps

$188.36

Live Like a Local in the Heart of Key West!brbrWelcome to your next luscious Vacay getaway—where history, culture, and island living come together just steps from your door! Located only 500 feet from the iconic Hemingway House and the Key West Lighthouse, and just two blocks from lively Duval Street, this centrally located cottage puts you within easy walking or biking distance to the best restaurants, galleries, nightlife, and attractions in town! Mallory Square, the Mel Fisher Museum, and the Key West Aquarium are all less than a mile away as well.brbrAfter a day of exploring, return to your private oasis and cool off in the sparkling plunge pool--Nestled into an enviously secluded outdoor space & is the perfect place for relaxing or entertaining! The home's interior features bold, bright, & inviting colors & furnishings--Creating a cozy and fun atmosphere throughout!brbrEnjoy the flexibility of two separate living rooms—each with smart TVs and comfortable seating—plus a fully equipped kitchen, ideal for preparing your 'Catch of the Day' or favorites from the local Seafood Markets. You can also grill up some dinner pool-side, while you enjoy a sunset cocktail at the outdoor bar. Upstairs, the primary bedroom offers a private bathroom and furnished balcony--featuring an ethereal spiral staircase that descends to the pool deck!brbrThe home includes full bathrooms on both floors, along with distinct sleeping areas for added comfort and privacy—ideal for families or a couples retreat. Additional amenities like high-speed WiFi, a private washer/dryer, and discounted Long-Term pricing make this the perfect place to soak up all that the Florida Keys have to offer!brbrDon't delay--Book your stay T O D A Y!!!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 p.m. to 8 a.m.brNo smoking is permitted anywhere on the premises.brLong-Term & Snowbird Renters WELCOME! - Please contact us for further details!brThis property is managed by Seven Keys Vacations by Casago.

Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House!

Key West, Florida, United States

Bed

Bath

Sleeps

$675.0

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented to Actor Matthew McConaughey and others. Expansive living room with vaulted wood ceilings and oversize couches leads to a large dinning room table that seats six. Gourmet kitchen with granite counters and lovely wood cabinets that focuses on the love of food and cooking. Indoor laundry area is located just off the kitchen for convenience. Large veranda overlooks the backyard sun-filled swimming pool and boat dock includes a table set and grills making outdoor cooking a breeze. Split floor plan makes the expansive master-suite with king bed, his and her sinks and Jazuzzi tub separate from two private guest bedrooms, one with king bed and the other offering a queen bed. Make Cameron's Luxury Waterfront Estate your next Key West Vacation Home and don't forget to bring your boat! Note: boat lift is owner's use only.brbr

LUXURY WATERFRONT ESTATE SEAWALL DOCKAGE & POOL

Key West, Florida, United States

Bed

Bath

Sleeps

$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

$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

$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

$161.02

*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.*brbrThis dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street.brbrNestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh seafood restaurants and dining spots right around the corner on Duval Street, you won't have to go too far to dive into it all. Take some time to wander through the unique shops to find that perfect prize to remember your trip. Do some stand-up paddleboarding or snorkeling while you're here.brbrSpend a relaxing afternoon by the shared pool. Connect to the free WiFi to book a reservation at a restaurant or cook a dish on the gas grill or convenient kitchen. Catch up with your favorite cable show in the central A/C while the private washer/dryer makes sure the laundry gets done. Chill out on the patio and slip into vacation mode. Two Dogs are welcome. brbrWhether you're taking in everything the beach scene has to offer, kicking back by the shared pool, or playing with your pups at the dog park, this Florida home makes it easy to let the stress melt away!brbr**This is a pet friendly unit with a two dog limit and a 35 pound weight limit for each dog.**brbrThis property is managed by Vacasa Florida LLC.

Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK

Key West, Florida, United States

Bed

Bath

Sleeps

$1725.51

Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include new carpet, updates to the upstairs bathrooms, and adding a waterfall to the pool. The interior is absolutely stunning with a gourmet kitchen, French doors throughout, and sunrooms to dive into your favorite book, yet stepping outside to the lush backyard will also be a treat. When days heat up, everyone can take a dip in the sparkling pool or simply lounge under the shade of the palms and banana trees as the chef of the group cooks up some burgers on the gas grill. Dine al fresco or gather with the whole family in the formal dining room to reminisce about the day's adventures. When the sun dips below the horizon, cozy up on the sectional sofa and play a movie on the TV with a bowl of popcorn. With so much fun to be had right at your fingertips, no one will want to leave this southern oasis!brbrLocated in Truman Annex, an exclusive private residential community in Old Town Key West, this home is situated on a small cul-de-sac just off Duval Street and close to great entertainment, dining, shopping, and attractions. When you want to venture out a bit, head over to the Key West Aquarium or Mallory Square, both sitting within walking distance of your front door. Little White House, the Key West Lighthouse, the Hemingway House, and Mel Fisher Maritime Museum are all great options as well within a few miles of home base. Don't forget to pop into some of the local restaurants and grab some seafood!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy 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.brThis property is managed by Seven Keys Vacations by Casago.

Southern snowbird-friendly house with pool, stunning backyard & great location

Key West, Florida, United States

Bed

Bath

Sleeps

$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

$242.67

House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexico. It has all the bars, restaurants, attractions and sunset celebration one could ask for. No need for a car.brThe Neely House has been a part of Key West History as was the Family who owned it for over 100 Years! When you enter the home you are greeted with ten foot ceilings,traditional wood floors and an open living and dining room that will make you want to put on your dancing shoes and salsa the night away. An oversize kitchen leads you to the second floor with four separate bedrooms and a traditional conch style porch just off the master bedroom to enjoy the sites of old Key West. The backyard is completely fenced and features a large wood deck that encompasses a beautiful 100 plus year old Spanish Lime Tree. This home allows you to truly experience the history and tradition of Old Key West.brNote: 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. If Key West closes to tourists due to COVID related travel shutdown, you will recieve 100% refund minus credit card fee of 3.5%. br

Stone Throw Famous Duval Street Location-No Contact Check-In

Key West, Florida, United States

4

Bed

Bath

10

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

6

Sleeps

$1891.88

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.

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Key West, Florida, United States

Bed

Bath

Sleeps

$2029.5

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.

The Joyrise House at Solaire Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$2519.19

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.

The Fairhaven House at Solaire Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$2059.55

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.

The Greenmoor House at Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$294.65

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…

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

Key West, Florida, United States

Bed

Bath

Sleeps

$178.8

This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood restaurants and best happy hours on the island…or walk to Duval street to experience the local music scene, bar hopping, restaurants and shopping…take in the famous Mallory Square sunset celebration…go fishing, snorkeling, jet skiing or relax on the beach. Several pools within walking distance. Located in a privately owned historic home. No need for a vehicle. brLofted bedroom has a queen bed and there is a full size sofa sleeper in the living room. The full kitchen is stocked with everything you need for cooking. 40 cable TV in the living room and WiFi throughout. Laundry is located outside the unit. Table and chairs for relaxing outside on the balcony.brClose to everything, yet quaint and quiet, you'll love your stay! We have 2 other units in our home, another one bedroom 1411765 and a 2 bedroom unit 1420448. br

Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.

Key West, Florida, United States

Bed

Bath

Sleeps

$315.32

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.

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

Key West, Florida, United States