Home Vacation Home Rentals By Owner In Key West, FL

Showing 820 Of 878 Vacation Rentals
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Exceptional(24)

$423.22

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Private Vacation Home

~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool awaits you. Later, you can cozy up to a bedroom of your choice. brbrThe first-floor queen ensuite bedroom includes a desk, dresser, ceiling fan and access to the pool. The second floor is home to three additional bedrooms. The first is a king suite with TV, wet bar, and walk-in/walk-through closet with access to the washer/dryer. Its ensuite bath has a large soaking tub with a laminar flow filler that fills from the ceiling, and a spacious walk-in shower with multiple heads. The room also provides access to a private balcony. The second is a queen suite with nightstands, ceiling fan, TV, dresser, and glass doors leading to the sun deck. The third bedroom on the second floor includes twin beds that may be converted to a king. This bedroom accesses a full bath from the hallway. It also has access to the second-floor balcony in front of the home that overlooks Fleming Street. This balcony wraps around the side of the house and connects to the sun deck. Its spiral stairs will lead you down to the pool area. brbrBack downstairs you will pass the half bath on your way to the open concept great room. Here you will find sunshine, happiness and the home’s living room and kitchen. Stainless steel appliances, a triple sink, and granite counters round out the gourmet kitchen. The adjoining living room has a queen sleeper sofa, plenty of seating for your family and friends, a large screen TV, ceiling fans, and storage. From this area you will also find table seating for six, a wet bar with wine fridge, and access to the pool area via the expansive wall of windows. This home embodies the Key West lifestyle and is yours to enjoy while here on the island. brbrBED CONFIGURATION: This home has 4 beautifully appointed bedrooms. A queen ensuite bedroom is located on the first floor for those who may not prefer stairs. Three additional bedrooms are located on the second floor. They include one king ensuite, one queen ensuite and one twin bedroom. The twin beds may be converted to a king size bed and have access to a full bath in the hall. brbrOUTDOOR AMENITIES: A small sitting pool spills into the larger pool and will cool you down after a day exploring the island. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. There is a deck and outdoor dining area for al fresco meals. brbrPARKING: There is designated parking for 2 vehicles in the carport.brbrLOCATION: Old Town, North of Truman. Many tourist attractions are located here as well as restaurants, shops, and galleries. Just 5 blocks to Duval Street or the Marina and walkable for those who like to park their car and chill. The neighborhood boasts historic homes, shotgun, and conch style homes.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 not allowed.brbrSMOKING: This is a non-smoking home. brbr***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***
Bed 4

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Bath 4

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Sleep 8

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Exceptional(176)

$278.81

/ Nightly
Private Vacation Home

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

Key West, Florida, United States

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West charm and contemporary touches. To explore the second-floor home, search for “Poinciana Treetop,” or book “Poinciana Paradise” to reserve the entire home for family or friends.brbrWalkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered front porch. Prepare meals in the bright and snug kitchen with built in corner hutch, open shelving, and gas range. With so many local dining options, you won’t even mind being without a dishwasher. The open living area includes brand new mini-split AC, ceiling fan and comfy couch. The primary bedroom includes an ensuite bath, TV, nightstands, closet, brand new mini-split AC, and ceiling fan. Not to be missed is the bedroom access to the lush outdoor area. Sun yourself in the shared yard or take a jaunt to the beach. When the day is over, you may find yourself relaxing under the stars and enjoying conversation with friends. brbrBED CONFIGURATION: The king bedroom has an ensuite bathroom with a mini-split AC and tub/shower combination. There is a sleeper sofa in the living room for a child or guest. brbrOUTDOOR AMENITIES: Open the French doors from your bedroom and step out onto the first-floor porch. The backyard features a shared gas grill, washer and dryer, lush garden, back deck with chaise lounge chairs, and outdoor dining set. *Please note this property no longer has a hot tub.*brbrPARKING: There is on-site parking for one small car as well as a bicycle rack for your convenience. 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***
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Bath 1

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Sleep 3

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Exceptional(169)

$300.14

/ Nightly
Private Vacation Home

~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.

Key West, Florida, United States

THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Key West activities, you won’t need a car, just a pair of sandals or a bicycle. Tucked down a quiet one-way lane, this casual home is comfortably furnished. It sits just a block and a half from Duval Street yet it’s oh so tranquil. As you enter the front door from your covered porch, you will be welcomed by natural light, sunny walls, and Florida furnishings. The living room opens to the dining area that leads to the kitchen. The living room houses a sofa, chair, split unit AC and a large screen TV. Open to the dining area, you will find table seating for four and eclectic splashes of art. The kitchen includes a full-size refrigerator, dishwasher, gas range, microwave and all the tools necessary to cook meals or prepare snacks. brbrThe bedroom is located off the living room. It’s soothing white walls are peppered with art. The room is cozy and comfortable, and includes dresser storage, a reading chair, bedside lamps, and a ceiling fan. A garment rack provides easy access to your clothing. You can enter the lushly landscaped, shared outdoor space from your bedroom. The snug bathroom with a tub/shower combination is more than adequate for rinsing off after a day in the sunshine. Homey and low-key, Solaris Cottage is a unique place to enjoy a laid-back vacation on beautiful Key West. brbrSOLARIS COTTAGE occupies the front section of this first-floor duplex home. SOLARIS GARDEN occupies the back section of this duplex home. For information on renting both parts of this duplex, please see SOLARIS PAIR-A-DISE. brbrBED CONFIGURATION: The queen bedroom is furnished with a dresser for storage, a ceiling fan and reading chair. brbrOUTDOOR AMENITIES: Open the doors from your bedroom and step out to the shared side deck under a giant Banyan tree. Step outside the kitchen door and you will find the shared infrared grill as well as the shared outdoor washer and dryer.brbrPARKING: There is no designated parking for this rental, however, there is usually parking available on nearby Petronia and Angela Streets. To avoid a parking ticket, please be sure that you don’t park in a spot labeled residential, as these are assigned to full-time residents.br brLOCATION: The property is on a tiny, one-way lane in Old Town, North of Truman Avenue and just a block and a half from Duval Street. Leave your car at home because you are just a short walk or bike ride to many tourist attractions, bars, restaurants, shops, and galleries including Mallory Square, known for breathtaking sunsets and performers. 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***
Bed 1

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Bath 1

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Sleep 2

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Exceptional(141)

$1988.08

/ Nightly
Private Vacation Home

~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!

Key West, Florida, United States

** Chavez House is available for 28 night minimum for the month of August ONLY. Live like a local! brbrTHE PROPERTY: By bringing the outdoors in, this home allows you to live like a true Floridian. The fenced yard provides you with privacy to enjoy your pool. Sun yourself on the lounge chairs or dine under the stars. And if that isn’t enough, you can enjoy life on the lanai. Read a book, take a nap, or keep an eye on the kiddos while they splash in the pool. Comfortable furnishings and a vaulted ceiling with tropical fan, make this a great outdoor gathering spot for family and friends.br brAs you enter the home’s first floor, you will find hardwood floors, the family room, dining room, kitchen, primary bedroom, and bath. Your king bedroom is to the left of the entry’s staircase. It is beautifully furnished, includes nightstands and bedside lamps as well as Dade County pine wall accents. A TV, ceiling fan and large dresser provide all the comforts of home. Its distinctive bath design allows you to open it to the kitchen or close it to use as your private ensuite. It includes a large vanity with dual sinks, a tub/shower combination and is adjoined to the pedestal sink room. The family room is to the right of the entry and leads back to the dining room and kitchen. The room is flooded with natural light, has plenty of seating for the family, a TV, and stunning wall art. Heading back towards the fabulous dining room, you will find seating for six and a sideboard for storage. From the DR you may access the lanai as well as the kitchen. Stainless steel appliances, white quartz countertops and a vaulted, shiplap-style ceiling add to the volume of this space. French doors lead to the pool and outdoor dining area. The convenient kitchen breakfast bar with seating for four, doubles as an island and includes a pass-through window to the lanai. It’s as easy as can be to prepare meals or snacks and enjoy them outdoors, Key West style! brbrAscend the beautiful wrap around staircase to the second-floor queen bedrooms and bath. The first bedroom is bright and cheery. The barn door closet and vaulted ceiling will charm you. Nightstands with bedside lamps, a wall TV, ceiling fan and dresser round out this room. The second queen bedroom is also bright and cheery and includes nightstands, bedside lamps, and a TV. Store your things in the louver door closet or open shelf dresser. Work or school from home in this room with a desk and task lighting. Your stay in this historic home will leave you with lasting memories of life in Old Town, Key West.brbrBED CONFIGURATION: The first floor includes a primary king bedroom and large hall bath with dual sinks and tub/shower combination. The second-floor queen bedrooms share a hall bathroom with vanity sink and tub/shower combination.br brOUTDOOR AMENITIES: The pool with waterfall feature is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Decking and lush landscaping surround the pool area where you can sunbathe, grill your dinner or lounge under the lanai.br brPARKING: No designated parking. Free street parking in the neighborhood. Note: Do NOT park in parking spaces marked as RESIDENTIAL or PERMIT ONLY. brbrLOCATION: Old Town north of Truman Ave. Many attractions, historic homes, restaurants, and shops are nearby. From here you can walk to the lure of Duval Street, read humorous epitaphs at the intriguing KW cemetery, and enjoy the Historic Seaport district.br brPETS: 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***
Bed 3

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Bath 2

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Sleep 6

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Exceptional(159)

$300.2

/ Nightly
Private Vacation Home

~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!

Key West, Florida, United States

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. To explore the first-floor home, search for “Poinciana Garden” or book “Poinciana Paradise” to reserve the entire home for family or friends. brbrWalkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered porch with a treetop view. Prepare meals in the bright and sunny kitchen with built in corner hutch, open shelving, and gas range. With so many local dining options, you won’t even mind being without a dishwasher. An open concept living area with vaulted ceilings provides natural light and adds to the airy ambiance of your vacation home. This area is cooled by a brand new mini-split AC and ceiling fan. The primary bedroom includes an ensuite bath, TV, nightstands, brand new mini-split AC, and ceiling fan. Stroll through its French doors onto the private porch and enjoy the Florida breeze with a delightful book. Sun yourself in the shared yard or take a jaunt to the beach. When the day is over, you may find yourself relaxing under the stars and enjoying conversation with newfound friends. brbrBED CONFIGURATION: The king bedroom has an ensuite bathroom with a tub/shower combination and a mini-split AC. There is a sleeper sofa in the living room for a child or guest. brbrOUTDOOR AMENITIES: Open the French doors from your bedroom and step out onto the second-floor covered porch. The backyard features a shared gas grill, washer and dryer, lush garden, chaise lounge chairs, and outdoor dining set.brbrPARKING: There is on-site parking for one small car as well as a bicycle rack for your convenience. 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***
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Bath 1

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Sleep 3

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Exceptional(6)

$244.98

/ Nightly
Private Vacation Home

Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking

Key West, Florida, United States

brWelcome to Banana Wind — Your Perfect Key West Retreat!brbrLocated in the charming Truman Annex Foundry Building, Banana Wind offers a spacious and stylish 2-bedroom, 2.5-bath townhome just steps away from the best of Old Town Key West.brbrThis beautifully maintained condo comfortably sleeps up to 6 guests with a king bed in the primary suite and two twin beds in the guest room (convertible to a king upon request). A cozy sofa bed in the living room provides extra sleeping space for your group.brbrPrime Location:brJust 3 blocks from bustling Duval Street, 2 blocks to the serene Truman Waterfront, and only half a mile from Fort Zachary Taylor Beach. Walk to restaurants, shops, nightlife, and historic sights — no car needed!brbrInside Your Home Away From Home:brbrFirst Floor: Bright and inviting living room with oversized windows, a sleeper sofa, and plenty of seating. Enjoy meals around the formal dining table for six, and prepare your favorites in the fully equipped modern kitchen with full-size appliances and all the utensils you’ll need. A convenient powder room completes this level.brbrSecond Floor: Relax in the spacious primary suite featuring a king bed, flat-screen TV, work desk, ample storage, and a private balcony perfect for morning coffee. The ensuite bath includes a shower and bathtub. Laundry facilities are also located on this floor.brbrThird Floor: The guest bedroom offers two twin beds (convertible to king), a workspace, generous storage, and a private ensuite bathroom.brbrOutdoor Perks:brEnjoy the fenced courtyard and front lanai with comfortable outdoor seating and a gas grill — ideal for unwinding after a day of exploring.brbrCommunity Amenities:brTake a refreshing dip in the shared pool, complete with lounge chairs and a restroom. Towels are provided inside the condo. One assigned parking space is included for your convenience.brbrNeed More Space brTraveling with a larger group Check out our sister properties, Unit 18 and Unit 20 (Southern Escape), located right next door with identical layouts and amenities.brbrBanana Wind is the ideal home base for your Key West getaway, combining comfort, convenience, and a prime location to help you experience all the island’s must-see spots.brbrBook now and start your unforgettable Key West adventure!
Bed 2

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Bath 2

Bath

Sleep 6

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$289.9

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Private Vacation Home

Monthly rental-1 level, 4-bed, 3 bath, quiet home, private sunny pool, parking

Key West, Florida, United States

Available for 28 night minimum stays only, due to Key West regulations. In high season (Dec.-April) If you are renting for one month only, the stay would start on the 1st and end on the day before the last day of the month to allow for things to be completed in between guests. If it's non high season the dates can be more flexible. The owner has a minimum rental age of 50 years old for the primary renter that will be in the home. The only pets allowed is a small, non shedding dog breed under 20 pounds and a pet fee of $250 per month would apply. A short term rental agreement would be signed.brNestled on a coveted corner lot on Eagle Avenue, this Mediterranean-style home is a true gem in the heart of Key West. A sun-drenched foyer opens to a spacious living area, perfect for both relaxation and entertaining. The updated kitchen boasts stunning Quartzite countertops, custom cabinetry, and modern finishes. With three generous bedrooms and three bathrooms, the home’s largest bedroom suite overlooks the sparkling pool and offers dual bathrooms for effortless morning routines. This large bedroom has a separate entrance by the patio with the table and couch. The 4th bedroom is outside and has a/c only. The 3rd bath is also outside with a shower curtain, see photos.brOutdoor living is a dream with a tropical fenced yard, lanai, al fresco dining spaces, and a refreshing 10ft x 30ft x 4.5 ft. deep pool surrounded by lush landscaping and ambient lighting. A versatile bonus space located outside next to the garage is currently set up as a bedroom. Additional perks include a garage for off-street parking and storage, an outdoor shower spigot in addition to the outdoor bathroom, central AC. Minutes from grocery stores, beaches, parks, the airport, and vibrant Old Town, this move-in-ready paradise captures the essence of Key West living. This home will suit all of your vacation needs. The floor plan is in in the photos but basically the large bedroom is overlooking the pool and just off the patio where the couch/table/chairs are. 2 of the bedrooms are inside and share a bath with shower, sink, toilet. The 4 th bedroom is in a guest room across the pool area that does have a/c, but also no heat. The bath for that room is outside attached to the home and next to the laundry area. It doesn't face anything but a fence and trees so it is private. It has a shower curtain but no door. The largest bedroom has an ensuite bath with the tub, walk in shower, 2 sinks, and 2 toilets. There are 3 walk in showers (one is in the bathroom outside by the pool) along with a separate outside nozzle to rinse off with. Bikes are not included but there are many places to rent bikes nearby. There is a driveway and a garage. You can park on the street too.
Bed 4

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Bath 3

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Sleep 4

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$270.08

/ Nightly
Private Vacation Home

Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches

Key West, Florida, United States

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Island Time on Washington — your ideal home base for a relaxed Key West getaway! brbr brbrThis welcoming pet-friendly 4-bedroom home in Midtown Key West is designed for comfort, flexibility, and easy island living. The property happily accommodates up to two dogs, each 85 lbs or less, so your four-legged family members can enjoy island time too. brbr brbrThe main house features three inviting bedrooms, one full bathroom, a bright living area, and a well-equipped kitchen perfect for meals at home. A separate private apartment adds valuable space and privacy for extended families or multi-generational groups, offering its own bedroom, bathroom, full kitchen, and private entrance—while still keeping everyone close. brbr brbrStep outside to your private tropical oasis, where a shimmering saltwater pool with optional heat invites long afternoons in the sun. With plenty of seating and space to relax or dine outdoors, it’s the perfect setting for unwinding after a day of island adventures. brbr brbrOff-street parking for up to two vehicles makes arrival effortless, though you may find yourself leaving the car behind thanks to the home’s central location. Higgs Beach, Smathers Beach, and Duval Street are all just minutes away, offering quick access to sandy shores, waterfront paths, dining, shopping, and Key West nightlife. brbr brbrComfortable, spacious, and thoughtfully arranged, Island Time on Washington is an ideal retreat for guests traveling together—pets included—while experiencing the very best of Key West. brbr brbrSLEEPS MAXIMUM OF 10 GUESTS: brbr brbrBedroom 1: King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: King Bed brbr brbrBedroom 3: Twin Trundle Day Bed brbr brbrBedroom 4 (apartment with outside access): Queen Bed, Smart TV (no cable/satellite TV), Two Loveseats (one pull-out queen bed), Kitchen brbr brbrLiving Room: Sofa, Loveseat, Chair, Smart TV (no cable/satellite TV) brbr brbrKitchens: Each Nicely Equipped (all things necessary to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Private Pool (optional heat ~85 degrees available Nov 1-Apr 30 for $30/night fee) brbr brbr- Outdoor Seating brbr brbr- Keurig, Toaster, Blender brbr brbr- Propane BBQ Grill brbr brbr- Off Street Driveway Parking for 2 Vehicles brbr brbr- Linens and towels provided brbr brbr- 0.7 miles to White Street Pier brbr brbr- 0.8 miles to Smathers Beach brbr brbr- 0.9 miles to Higgs Beach brbr brbr- 1.0 miles to Upper Duval Street brbr brbr- 1.1 miles to Southernmost Point brbr brbr- 1.7 miles to Key West Historic Seaport brbr brbr- 2.0 miles to Lower Duval Street brbr brbr- 2.2 miles to Mallory Square Sunset Pier brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrFor Sale: This property is currently listed for sale, and guest bookings are limited to stays with check-out dates within the next 90 days. brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to two friendly and well-behaved dogs 85 LBS or less each will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited on the premises to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, four exterior security cameras monitor the front door, both sides and rear/pool area. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
Bed 4

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Bath 2

Bath

Sleep 10

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$1564.57

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Private Vacation Home

Casa De Cubana | New! Cuban-Style Home Near Duval

Key West, Florida, United States

Casa De Cubana | New! Historic Cuban-Style Home Steps from Duval StreetbrbrDiscover the charm and elegance of Key West at Casa De Cubana, a newly constructed 2-bedroom, 2.5-bathroom home that blends the rich history of Old Town with modern comforts. Located just half a block off the iconic Duval Street, this single-story elevated home draws inspiration from early 20th-century Cuban architecture, offering a unique and stylish retreat in the heart of Key West. With it's prime location and modern amenities, Casa De Cubana ensures tranquility while keeping you close to all the vibrant attractions of the island.brbrThe Ambiance: brStep into a beautifully crafted home where classic Cuban elements meet contemporary luxury. Designed with meticulous attention to detail, Casa De Cubana offers a spacious, open-concept floor plan that creates a seamless flow between the living areas. brbrHighlights include:br- A fully equipped kitchen with stainless steel appliances and ample counter space for culinary creativitybr- Two serene bedrooms, each with queen beds and en-suite bathrooms, offer comfort and privacybr- An elegant living area that invites relaxation and enjoymentbr- Lush outdoor landscaping surrounding a peaceful patio and a private heated pool, perfect for unwinding after a day of explorationbrbrWhether you're lounging indoors or entertaining on the patio, Casa De Cubana provides an inviting space to relax and create lasting memories.brbrGuest Access: brEnjoy a seamless arrival experience with contactless check-in. You'll receive personalized access details prior to your stay, allowing you to head straight to the property and start your vacation without a hitch. Our local team is available for any assistance or recommendations during your stay.brbrLocation Highlights:brNestled in the heart of Key West, Casa De Cubana is only a short walk from the vibrant Duval Street, where you can enjoy world-class dining, lively nightlife, and shopping. Whether you're strolling through the historic district, relaxing on the nearby beaches, or visiting iconic landmarks like the Southernmost Point, everything Key West has to offer is right at your doorstep. This prime location allows you to experience the best of both worlds—seclusion and convenience.brbrTransportation Tips:brGetting around Key West is easy from Casa De Cubana. With the property's central location, you can walk or bike to most of the island's popular attractions. For further adventures, taxis, rideshare options, or golf cart rentals are available nearby. Public transportation is also accessible for exploring beyond Old Town.brbrOther Things to Note:br- Central air conditioning for year-round comfortbr- On-site parking for your conveniencebr- Washer and dryer available for guest usebr- Guests must be 25 years of age or older to reserve this property.br- Pets Considered! Guests must request approval prior to booking — $20/per pet per night fee.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.
Bed 2

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Bath 2

Bath

Sleep 4

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$1385.21

/ Nightly
Private Vacation Home

~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking

Key West, Florida, United States

THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. As you enter your portal to paradise via the custom iron gecko gate, you will immediately feel as if you have left all your cares behind. You will be greeted by the home's stunning French doors, pool, lounge area and second story balcony. brbrAlways wanted to step from your bedroom into the pool You can do it from Cloud 9! Both first floor king bedrooms with ensuite baths are just steps from the pool and overlook the garden area. They share a wet bar for easy access to refreshments by the pool. Through the back door of each bedroom, you will find the rear patio, a charming swing and washer and dryer. Travel up the wide staircase that separates the first-floor bedroom suites, to the second floor. The third bedroom, ensuite bath and private balcony are also located on the second floor. The open concept main living area, dining area, and gourmet kitchen are spacious. The covered front balcony overlooks the pool, and the rear balcony is an extra outdoor treat. The main living space is flooded with natural light, comfortable white furnishings, and eclectic art. brbrThere is plenty of room to entertain, enjoy game night, prepare meals, or simply relax and unwind. Your family and friends will not only be indulged in comfort, but they will enjoy the privacy of their own spaces at night. It's time you experience the joy of vacationing on Cloud 9! brbrBED CONFIGURATION: Two spacious king bedrooms with ensuite baths are on either side of the first-floor entry. The third bedroom with ensuite bath is on the second floor and is furnished with two twin beds that may be converted to a king. All bedrooms have TVs and closets. The living room sectional is also a sleeper sofa for one additional person. brbrOUTDOOR AMENITIES: The beautiful pool and several seating areas provide plenty of space for family or guests. A small rear patio and porch swing offer a quiet place to read or meditate. You won't feel cramped in this piece of heaven! The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. brbrPARKING: Pull right up to the whimsical, iron gecko gate and enjoy your private off-street parking space for one small car. brbrLOCATION: Old Town, just 1/2 block from Duval Street. Close to restaurants, bars, shops, and tourist attractions. Just steps from Fausto's, Key West's family-owned grocery store where you may purchase anything from pantry staples to gourmet food and wine. The neighborhood also boasts historic, shotgun and conch style homes. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly.)brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult. br***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not present inside the property nor at the pool area.***br***Managed by Historic Key West Vacation Rentals***
Bed 3

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Bath 3

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Sleep 7

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Exceptional(39)

$276.5

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Private Vacation Home

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrCOLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE KEYS has a layout that optimizes privacy for your group, with each bedroom on its own floor with a private bathroom. This townhome also offers a private outdoor courtyard, off-street parking, and access to a shared pool. Combined with Last Key Realty's Five Star Guest Services, COLORS OF THE KEYS provides the perfect setting for your group to experience a colorful Key West vacation.brbrSmoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe landscaped community pool is located just across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrTHE LIVING AREA...brbrUpon entering COLORS OF THE KEYS, you’ll immediately see where this home gets its’ name. The open living area, with tasteful accents of coral and aqua, boasts 11-foot ceilings and double French doors that allow plenty of natural light to flood through. The living room features a large flat screen TV and comfortable seating, including a plush sofa that pulls out to a Queen sleeper to accommodate extra guests. There's also a convenient powder room located on the first floor. The kitchen is fully equipped with stainless steel appliances and all of the tools you’ll need to prepare a meal from home. The indoor dining table seats six comfortably. The private courtyard out front is the perfect place to experience the island breezes, and is complete with a gas BBQ grill and patio furniture.brbrTHE ACCOMMODATIONS...brbr** Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a shower and tub combo.brbr** Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbrEach floor closes off with its own separate door as well for extra privacy.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Propane BBQ Grillbr** Assigned Off-street Parking for 1 CarbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 2

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Bath 2

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$1184.74

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Private Vacation Home

**THE SOPHISTICATED SANDPIPER @ OLD TOWN** Home & Pool Near Duval + LAST KEY SER

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrA lavish Key West vacation deserves an equally lavish home where your group can flock together. THE SOPHISTICATED SANDPIPER offers spacious living areas that invite everyone to gather and relax, while 3 private bedrooms with en-suite bathrooms offer a peaceful perch when it’s time to recharge. You'll be spoiled with the sparkling saltwater pool and inviting lounge area that creates an ideal setting for sunny afternoons and breezy island evenings. Centrally located within walking distance of world-famous Duval Street and the Historic Seaport, THE SOPHISTICATED SANDPIPER is the perfect nest for groups looking to experience Key West in style. Best of all, your stay includes Last Key Realty’s renowned Guest Services & In-house Concierge, known for providing memorable vacation experiences.brbrTHE LOCATION...brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a stroll or ride your bike down to the best of Key West, three blocks down Olivia St to hit local favorites like Moondog Cafe, Martin's, and Nine-One-Five. Just a few blocks down Windsor Lane and you'll be at BO's Fish Wagon or Schooner Wharf.brbrTHE LIVING AREA & KITCHEN...brbrTHE SOPHISTICATED SANDPIPER features soaring ceilings and sleek, modern furnishings that set the stage for a premium stay. The living area is bathed in natural light thanks to double sets of floor-to-ceiling glass sliders, creating a bright and airy atmosphere all day long. Relax in the plush living room furniture — centered around a large Smart HDTV — which seamlessly transitions into the state-of-the-art kitchen. Whether you’re crafting a cocktail at the fully-equipped wet bar or preparing a home cooked meal using the high-end appliances, this open-concept space is designed for effortless entertaining. Dine together at the six-person table or grab a quick bite at the three-seat breakfast bar. A convenient powder room is located in the hall.brbrTHE PRIVATE SALTWATER POOL...brbrBeyond the double sets of sliding glass doors lies the crown jewel of the property: your own private tropical oasis. Surrounded by a privacy fence and framed by lush, exotic landscaping, this secluded sanctuary is the ultimate gathering spot for your group. Spend your afternoons lounging on comfortable chaises — easily moved to follow the sun or escape into the shade — beside a heat-optional saltwater pool. When evening falls, ignite the large propane grill for a poolside BBQ, followed by an al fresco dinner at the elegant five-person dining set.brbrTHE ACCOMMODATIONS...brbr** First Floor Bedroom: Two Twins OR One King bed and an en-suite bathroom with a walk-in shower.brbr** Second Floor Master Bedroom: King bed, private balcony, and an en-suite bathroom with dual sinks and a walk-in shower. brbr** Second Floor Guest Bedroom: Two Twins OR One King bed, private balcony, and an en-suite bathroom with a shower and tub combination. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Backyardbr** Private Saltwater Pool with Available Pool Heatbr** Propane BBQ grillbr** Off-Street ParkingbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Consideredbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.brbrNEED MORE SPACE...brbrLast Key Realty manages the neighboring townhome, THE ELEGANT EGRET, along with a number of other townhomes in this intimate complex. Inquire for details!
Bed 3

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Bath 3

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Sleep 6

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Exceptional(29)

$212.55

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Private Vacation Home

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

Key West, Florida, United States

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.
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Bath 1

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Exceptional(5)

$2026.88

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Private Vacation Home

The Dreamside House at Lunara Bay

Key West, Florida, United States

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.
Bed 8

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Bath 8

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Sleep 16

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Exceptional(14)

$656.95

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Private Vacation Home

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

Key West, Florida, United States

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***
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Bath 2

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Exceptional(23)

$284.04

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Private Vacation Home

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

Key West, Florida, United States

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***
Bed 2

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Bath 2

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Exceptional(25)

$500.16

/ Nightly
Private Vacation Home

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

Key West, Florida, United States

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***
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Exceptional(6)

$734.53

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

Key West, Florida, United States

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
Bed 3

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Bath 3

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Sleep 7

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Exceptional(5)

$137.05

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Private Vacation Home

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

Key West, Florida, United States

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.
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Bath 2

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Sleep 4

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Home Most popular vacation rentals in Key West