Vacation Rentals By Owner In Key West, FL

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Geiger Suite is located on the 3rd floor and offers a king and a full bed for up to 4 guests in this 2 bedroom suite with both pool and tropical garden views from the shared deck with lounge furniture. The king bed is located in the spacious main room, while the full bed occupies the second room that provides access to the PRIVATE full bathroom with a shower. The sloping ceiling over the bed makes for a cozy nook in your nighttime retreat. brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$297.41

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brEmbrace your inner author in the fabulous open plan Hemingway Suite that is located on the 2nd floor. Sink into slumber in your luxurious king bed, featuring Miami Dade pine walls and a PRIVATE bathroom with a shower. Soak in the Key West vibe from your inviting deck just outside of the room.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$194.38

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Whitehead Room is located on the 2nd floor and offers a queen bed. Enjoy your privacy in this location that is accessible from the back deck with lounge furnishings. Dade County pine walls and a PRIVATE bathroom with a tub/shower combination complete the cozy space. This room connects to the Truman Room. brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$284.23

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Flagler Room, located on the first floor, is a delightful place to decompress at the end of a fun day. Enjoy your slumber on your king bed, savor a cup of keurig coffee, and enjoy a show on the flat screen TV. This room also offers a PRIVATE wheel-in shower for easy access.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$188.76

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Simonton Room is located on the 1st floor and offers a plush king bed. Indulge in this lovely modern setting that offers a spacious PRIVATE bathroom with a shower/tub combination. Unwind and enjoy your flat screen TV and sip on a beverage from your mini-fridge. brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$330.19

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas reside on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe soothing Cornish Suite is located on the 3rd floor and offers two bedrooms, suitable for up to 4 guests. The first room offers a plush king bed, a sitting area and mini-fridge. The second bedroom features a double bed and provides access to the full PRIVATE bathroom with shower. The sloping ceiling over the bed makes for a cozy nook in your nighttime retreat. You will find an outdoor deck with lounge furniture just outside of the room.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

CORNISH SUITE @ Inn on Fleming ADULTS ONLY 3rd Floor 2 BR /Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$191.05

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Gato Room is located on the 2nd floor and offers a queen bed. This well-lit room features plush furnishings and includes a flat screen TV, mini-fridge, and a PRIVATE bathroom with a combination tub/shower.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$293.67

Welcome to Cozy Key West Cottage !!!brA REAL ISLAND GATAWAY IN KEY WEST!!!brbrStay just around the corner from Duval Street and walk to everything Key West has to offer. brAfter a day out, relax in your own private space in a great Old Town location.brbrPerfect for two guests who want to be close to everything.brbrNested in the heart of Key West, The Cozy Key West Cottage, welcomes you to a sanctuary of comfort and convenience. brbrAs your host , we're delighted to extend our warmest greeting and ensure your stay is nothing short of exceptional.

Apartment

Sailor`s cabin - Old Town - Walk to Duval !

Key West, Florida, United States

Bed

Bath

Sleeps

$212.55

STEPS TO IT ALL...brPeaceful surroundings of lush tropical foliage and picturesque white picket fences invite you into this charming 2 bed, 1.5 bath townhome located in the prestigious and highly coveted community of Truman Annex. Tucked away down a quiet pedestrian lane, you'll have all of the privacy of a gated community that is also just steps from Mallory Square, Duval Street and the many unique attractions Key West has to offer.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brUnwind in Paradise in this inviting townhome just steps from it all. Enter the delightful private porch with plush seating for 3 and toss your worries aside when you open the front door to your inviting sanctuary. The modern, fully-equipped kitchen greets you first, offering every tool and appliance you need to prepare your culinary concoctions for your favorite people. A kitchen bar seats 3 people and is adjacent to the dining table for 4. The open layout next invites you into the living area which boasts the comfort of multiple seating options, a large flat screen tv and two sets of french doors for welcoming cool island breezes inside. A convenient half bath is also located in the living area. Tropical decor with a ceiling fan creates a captivating atmosphere that leaves you refreshed on a warm summer’s day. There is a sleeper sofa in the living area for 2 additional guests.brbrSLEEPING ARRANGEMENTS...brTravel up the stairs to two guest rooms when you're ready to rest and refresh for the next day's adventures. The primary bedroom features a queen bed with a large flat screen tv, an overhead fan, abundant closet space and a delightful private balcony that overlooks the charming neighborhood lane, perfect for your morning latte or evening liqueur. The second bedroom is furnished with two twin beds that can be converted to a king, a flat screen tv, overhead fan, large closet and windows with plantation shutters. The two bedrooms share the hallway bathroom equipped with twin vanities and a deep tub/shower combination. There is a queen sleeper sofa in the living area.brbrOUTDOOR LIVING...brWalk through the living area french doors to your private outdoor area with seating for 4, which is the perfect 5 o'clock happy hour retreat as the sultry breezes soothe your soul. Take a stroll through this attractive community which is just right around the corner from Fort Zachary Taylor State Park, Harry Truman’s Little White House and Truman Annex’s Waterfront Park. Swimming in the heated community pool is a great way to wash off the day and it's just around the corner from the unit. There is a cabana with restrooms in the pool area and plenty of lounging chairs for your sunbathing pleasure.brbrPARKING...brThis home does offer covered parking for one vehicle. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.brbrPETS...brThis is not a pet friendly home. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). 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 stock your fridge!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!

Key West, Florida, United States

Bed

Bath

Sleeps

$2026.88

Summary:brbrDiscover a luxurious new waterfront home, 8 spacious bedrooms and a private pool at Lunara Bay - a collection of 26 Luxury homes in a gated community! . This stunning home offers exceptional amenities, including free gym access and ample living space perfect for relaxation and entertainment. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy 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.brbrbrbrThis property features eight bedrooms, each with a king bed and ensuite bathroom.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 Dreamside House at Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$284.04

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Step inside the white picket fence and enjoy your private escape. Surrounded by lush greenery and palm trees, this home with modern amenities is tucked into a charming, historic neighborhood. From here you can walk to many attractions Key West is notable for including bars, restaurants, and shops. Snap a photo at the Southernmost Point marker or grab lunch on Duval Street. When you are done touring the island, come home and enjoy a cocktail on the covered porch. brAs you enter the home, you will be struck by its hardwood floors and natural light. Upscale lighting and unique art embellish the living space. Both bedrooms are in the hall and are comfortably furnished. Head towards the updated kitchen and you will find the first of two full, updated baths. This tub/ shower combination with glass slider and large, single vanity is also home to a full-size washer and dryer. The beautiful kitchen is a chef’s delight. It is adorned with an island with bench seating, stainless steel appliances, slide-in gas range, and quartz countertops. White cabinets, a farmhouse sink, and all the conveniences of home are at your fingertips. A vaulted ceiling and recessed lighting enhance the open feeling of the room. The dining room with seating for four, is located just off the kitchen. Beyond the dining room is your family room and second full bath with pedestal sink and walk-in shower. The family room is comfortably furnished and has plenty of natural light. From here you can watch late night TV on the big screen without waking your kiddos or guests. A full glass panel door provides access to the pool area. Complete with a waterfall feature, the saline pool is oh so relaxing. Weather you are cooling off after a day of exploring the island or simply sunbathing, this area is private and comfortable. If you are looking for a convenient ‘locals’ area with great access to dining, look no further. Inn Cogneato is waiting for you!br brBED CONFIGURATION: Two queen bedrooms are located at the front of the home. Each is adorned with night stands, bedside lamps and either closet or dresser storage.br brOUTDOOR AMENITIES: The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Relax in the poolside lounge chairs. A propane grill and dining table are provided for your outdoor enjoyment.br brPARKING: No designated parking space but there is free street parking in the neighborhood. brbrLOCATION: Historic Old Town in Bahama Village, a vibrant and diverse neighborhood settled in the 1800s by families from the Bahamas. North of Truman Ave, this home is within walking distance to the Southernmost Point, and Duval Street. Several shops and restaurants are nearby including Bésame Mucho, Blue Heaven, Santiago’s and La Crêperie. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.br br***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***

~ INN COGNEATO ~Experience island life in a private oasis with heated pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$500.16

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished duplex home comes with Key West charm and contemporary touches. Walkable to many shops and attractions, you will feel like a local in no time. Only two blocks to Duval Street, you can relax and enjoy your time here, whether you select the upper or lower floor of this home.br brThe entire house includes a total of two bedrooms and two bathrooms. Each floor has a king bedroom, with brand new mini-split AC, an ensuite bath and tub/shower combination. There is a living room sleeper sofa on each level for a child or additional guest. From the lower-level bedroom, you can access the shared outdoor area via French doors. From the upper-level bedroom, you can access your covered porch via French doors. brbrYou will find the open concept living areas cool and inviting, with brand new mini-split AC's. The living rooms are comfortably furnished and awash in soothing colors. Cooking is a breeze in this amply equipped kitchen with corner cabinetry, open shelves, and gas range. Note: neither kitchen has a dishwasher. The home has several windows which allow natural light to filter through. The second floor includes vaulted ceilings, adding to the airy feel of the residence.brbrIf you only need to book one of the two spaces, please explore the first-floor home by searching for “Poinciana Garden” or the second-floor home by searching for “Poinciana Treetop”. No matter which you choose, you will surely enjoy your Key West vacation! brbrBED CONFIGURATION: Each king bedroom has nightstands, a TV and ensuite bathroom, mini-split AC with a tub /shower combination. There is a single person sleeper sofa in each unit, for up to 6 guests total.brbrOUTDOOR AMENITIES: Open the French doors from your bedroom at Poinciana Garden and step out onto its first-floor porch. The French doors off the bedroom at Poinciana Treetop lead to your covered second floor porch. In the back yard there is a shared gas grill and washer/dryer, lush garden, chaise lounge chairs, and outdoor dining set. *Please note this property no longer has a hot tub.*brbrPARKING: If renting both the upper and lower levels of the home, there is on-site parking for two smaller cars (one space per floor), as well as a bicycle rack for securing your bikes. Please note this home is on a tiny one-way lane. brbrLOCATION: Historic Old Town, North of Truman and 2 blocks from the excitement of Duval Street. A majority of the best Key West attractions are located here as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch style homes. You will enjoy being right in the middle of everything!brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!

Key West, Florida, United States

Bed

Bath

Sleeps

$656.95

THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are not far from the excitement of Duval Street in this home but far enough away to enjoy peace and quiet. This home consists of BOTH sides of a duplex.brbrThis duplex is unpretentious and comfortably furnished. There is sleeping space for six via 2 king beds and a queen sleeper sofa. In addition, each bedroom has an ensuite bath with pedestal sink and walk-in shower. The living rooms are off the dining areas and are easily accessible to the kitchens. The kitchens are stocked with everything you need for meal or snack prep. All you need to do is purchase groceries from nearby Fausto’s Food Palace. If you prefer, there are wonderful restaurants within walking distance of the homes. Wall AC, ceiling fans, TVs, and solid surface floors help make these homes quite comfortable. You can enjoy the private hot tub and large pool as well as outdoor dining areas and lounge chairs. Gas grills and two washers and dryers are also available to you. Vacationing with friends is great but vacationing with friends in your own private dwellings is even better! brbrCasablanca Grande consists of both sides of a duplex, each having their own entrance.brbrBED CONFIGURATION: King size beds and cotton duvets are in each bedroom. Casablanca Nightly has a queen sleeper sofa for extra guests.brbrOUTDOOR AMENITIES: This is a spacious vacation rental with a private 20‘x10’ pool and hot tub! The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Well-manicured grounds along with the wonderful outdoor areas set this property apart from others. Cook up your catch of the day on the gas grills and enjoy outdoor dining under the stars. brbrPARKING: Off-street parking is available for 2 cars, one per unit.brbrLOCATION: Historic Old Town, North of Truman Avenue and close to The Meadows, a residential district. Walk to Duval Street in 15 minutes or take a 5-minute bike ride to Higgs Beach or the Southernmost Point. Fausto’s Food Palace, The Best Coffee in Town, Bayview Park, and the Key West Cemetery are also just a short walk away.brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property. brbr***Staying for a month or longer Request a quote for a minimum of 28 nights to see our discounted monthly rates.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$263.56

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe Truman room is located on the 2nd floor and offers a cozy space with a queen bed and a PRIVATE shower bathroom. Perfect for a weekend getaway for two, this peaceful refuge connects to the Whitehead Room, providing additional space for friends or family traveling together for that special Key West vacation.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

TRUMAN ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$284.68

CAPTIVATING CLASSIC REVIVAL CHARM...brBuilt in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. Whether you're looking to hook your catch of the day, visit upscale art galleries, or swim with the dolphins, let us be your home away from home in paradise. br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brThe magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating, where you are immersed in the unique sights and sounds of our charming neighborhood. The spacious kitchen, dining and cozy living areas are located on the main level of the inn. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical heated pool featuring a soothing and relaxing waterfall. Indulge yourself with a favorite novel or explore the internet with free Wi-Fi. All of our rooms include an ensuite bathroom, Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker and a mini-fridge, countertop ice machine, as well as tropical garden views. Our concierge services can advise you about all the things to do, including reservations to snorkel, kayak in the mangrove channels, or relax on an evening sunset sail. brbrSLEEPING ARRANGEMENTS...brThe elegant Mallory Suite is located on the 1st floor and offers a dreamy king bed and beautiful furnishings. Surrender to a blissful sleep in your luxurious bed, wash off the day in your PRIVATE shower/ tub combination bathroom, and sip on your morning coffee in private with your dedicated patio entrance.brbrOUTDOOR LIVING...brFind your serenity and let your mind melt, listening to the soft rush of our pool waterfall. Enjoy cozy conversation and frosty beverages under the shaded pool tables, surrounded by lush foliage and sultry island breezes. Stroll through our garden that envelops you in lush mature landscaping and soothes your soul with tropical breezes. Bikes are available to rent for your outdoor adventures. brbrPARKING...brWe do not have our own parking but there is plenty of free on-street parking. Please refrain from parking in spots marked resident permit. brbrPETS...brThis is not a pet-friendly inn.brbrDISTANCES TO BEACHES...brSimonton Beach...0.8 mibrFort Zachary Taylor...1.5 mibrSouth Beach...1.2 mibrHiggs Beach...1.5 mibrSmathers Beach...2 mibrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrBE OUR CHERISHED GUEST...

MALLORY SUITE @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$203.6

This Beautiful one bedroom one bathroom condo was formerly a two bedroom opened up to create a spacious living area. The same square footage as a 2 bedroom. The condo is fully furnished and perfectly located in the Truman Annex, a gated community of private homes and condos within two blocks of Duval Street and Ft. Zachary Taylor State Park (best beach in Key West). This First Floor condo is a part of the Shipyard complex and is located in a very secluded area. The decks and gardens are totallybrbrThis Beautiful one bedroom one bathroom condo was formerly a two bedroom opened up to create a spacious living area. The same square footage as a 2 bedroom. The condo is fully furnished and perfectly located in the Truman Annex, a gated community of private homes and condos within two blocks of Duval Street and Ft. Zachary Taylor State Park (best beach in Key West). This First Floor condo is a part of the Shipyard complex and is located in a very secluded area. The decks and gardens are totally private with no condos behind it so no one will be glaring over or down at you. Few condos can offer this privacy in the Annex.brbrParking notes: There is 1 designated parking space. Vehicles over 18' long or 80' wide are not allowed on property. All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass .All others will be subject to ticketing and/or towing.

Renovated Corner Unit

Key West, Florida, United States

Bed

Bath

Sleeps

$734.53

Renovated 3BD/3BA with bonus room.. This home is located in the prestigious Casa Marina neighborhood.Featuring impact doors and windows, updated kitchen, outdoor dining and entertainment area. Large new pool and waterfall , mature landscaping, and is fully fenced for privacy. Walking distance to Higgs beach, The Casa Marina hotel bars and restaurants, Salute on the Beach, Louie's backyard, Tennis/pickle ball courts, Volley Ball Courts and the most beautiful sunsets. brbrRenovated 3BD/3BA with bonus room.. This home is located in the prestigious Casa Marina neighborhood.Featuring impact doors and windows, updated kitchen, outdoor dining and entertainment area. Large new pool and waterfall , mature landscaping, and is fully fenced for privacy. Walking distance to Higgs beach, The Casa Marina hotel bars and restaurants, Salute on the Beach, Louie's backyard, Tennis/pickle ball courts, Volley Ball Courts and the most beautiful sunsets. brbrWalking distance to Higgs beach, The Casa Marina hotel bars and restaurants, Salute on the Beach, Louie's backyard, Tennis/pickle ball courts, Volley Ball Courts and the most beautiful sunsets.brbrSelf check in, Lockbox on property. brAccess to the beach, tennis/pickle ball courts, Volley Ball Courts and more brbrRenovated 3BD/3BA with bonus room.. This home is located in the prestigious Casa Marina neighborhood.Featuring impact doors and windows, updated kitchen, outdoor dining and entertainment area. Large new pool and waterfall , mature landscaping, and is fully fenced for privacy. Walking distance to Higgs beach, The Casa Marina hotel bars and restaurants, Salute on the Beach, Louie's backyard, Tennis/pickle ball courts, Volley Ball Courts and the most beautiful sunsets. brbr4 miles from airportbrWalk to the beach

3 bedroom with living room and sitting room and a pool just 2 blocks from Higgs beach

Key West, Florida, United States

Bed

Bath

Sleeps

$137.05

Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Club with two community pools and a spacious clubhouse perfect for a home away in the tropics. A quick ride will get to Downtown Key West, to the world famous Duval St were you can enjoy dining and shopping. The house has two bedrooms with queen size beds on the 2nd floor that share a full bath on the main floor. You have an open style kitchen and a spacious living/dining room.brbrbrJust a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Club with two community pools and a spacious clubhouse perfect for a home away in the tropics.brA quick ride will get to Downtown Key West, to the world famous Duval St were you can enjoy dining and shopping.brThe house has two bedrooms with queen size beds on the 2nd floor that share one bathroom. On the main floor you have an open style kitchen and a spacious living/dining room.brYou will have a washer & dryer, central heat and A/C, ceiling fans, flat screen TVs, cable, wireless high speed internet, microwave, blender, toaster, coffee maker, fully equipped kitchen. All bedding, linens and towels are provided, and interim housekeeping is available. Also includes access to 2 community pools and fitness center.

2 bedroom Town home in a gated community with a resort sytle pool.

Key West, Florida, United States

Bed

Bath

4

Sleeps

$874.92