GORGEOUS COASTAL FAMILY ABODE... Modern luxury surrounds you as you enter this stunning renovation that welcomes a large family to gather and unwind in a beautiful coastal setting. This exquisite home boasts 5 bedrooms with 3 custom ensuite bathrooms and an additional fourth shared bathroom for your traveling crew in a perfect Midtown location which is only a brief walk to 2 pristine beaches! Enjoy a dedicated pedestrian/exercise path, dog park, beachfront dining and tennis/pickleball courts nearby. This spacious beauty is your perfect retreat in paradise. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. DETAILS AND AMENITIES... An open concept floor plan with stunning coastal decor delights your senses and sets the stage for a magical getaway. Luxuriate with loved ones in the modern great room with cushioned seating and a large wall-mounted TV. The generous adjacent kitchen overlooking the pool offers state of the art appliances and tools. The kitchen island with seating is ideal for breakfast conversations and the pass through window with seating invites peaceful enjoyment with a view of the pool area. Break bread with your crew in the dining room that comfortably seats 8. A full size washer/dryer closet is located downstairs. This home is equipped with YouTube TV streaming. SLEEPING ARRANGEMENTS... Downstairs: A primary king bedroom with ensuite bathroom resides on the main floor. Bask in your ultramodern double vanity and walk-in glass door rain shower as you wash away your cares. Open the sliding doors to your delightful outdoor sitting area under swaying palms and sultry breezes. The second bedroom offers a queen bed and the third bedroom is outfitted with a trundle bed (2 twin beds). A full bathroom with a shower/tub combination is located in the bedroom hallway. Upstairs: Travel upstairs to a fabulous bonus space, perfect for a cozy nook to read on the couch or catch up with work at the writing table. The second primary king bedroom is equipped with a walk-in closet, a sitting area for two, a contemporary ensuite bathroom with double vanity and walk-in glass door rain shower. Open your doors to the porch, perfect for sipping on coffee. The second king bedroom upstairs also offers an ensuite bath with glass door walk-in rain shower and single vanity. All bedrooms feature TVs, closets and clothing dressers. OUTDOOR LIVING... Situated on a corner parcel, this home is a veritable outdoor oasis, offering multiple covered patios, a maintenance free green space, a large sparkling heated pool with loungers, a shaded outdoor sectional and a dining table with seating for 6. Lush landscaping envelops your island soul and quiets your mind for hours of serenity and bliss. PARKING.... This home offers covered parking for your vehicle. PETS... This home considers dogs (NO CATS) only. Please include the size and breed when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival! BOOKING DATES... This 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. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). EASE ON DOWN TO WONDERLAND...

***PARDON OUR DUST! This building is being re-roofed the week of 5/27/25. We have discounted the home to offset any inconvenience. The unit will be fully accessible but there could be some noise, and construction crews will be present from 8-6 Mon through Fri. CHARMING 2ND FLOOR CONDO IN STUNNING "SHIPYARD" COMMUNITY OF TRUMAN ANNEX… Delight in this cozy gem of southernmost island living, a 2 bedroom, 1 bath second floor dwelling with a balcony that overlooks verdant landscaping and a sparkling shared pool! Slide on your comfiest sandals and immerse yourself in the excitement of Duval Street, just 2 blocks away. You are walking distance to the island's hot spots: Fort Zachary State Park Beach, The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly "Sunset Celebration". ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Enter this light and airy open living area that is colorfully and tastefully decorated to ease you into a sense of well-being and tropical tranquility. You and your loved ones will enjoy a cool respite after a day in the sultry sun, sharing relaxed conversation on the cozy furnishings or decompressing with your favorite movies on the wall-mounted TV. The fully equipped and well-stocked kitchen will inspire you to practice your culinary skills, complete with granite countertops, stainless steel appliances and all the tools a chef will need. Dine or play your favorite board game at the table for 4. SLEEPING ARRANGEMENTS… Slip into a peaceful sleep in one of the two bedrooms with plush queen beds. Both rooms offer flat screenTVs, cooling ceiling fans, clothing dressers and nightstands with power ports. The shared bathroom has been updated with a walk-in shower and there is a full washer/dryer closet for your convenience. OUTDOOR LIVING… Open the French doors of the coastal living room to your balcony with umbrella table and chairs, a superb spot for morning coffee or dining outdoors. a second balcony resides just off the kitchen, with a lounge chair for napping or reading your favorite novel. The Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun. PARKING... This home does offer parking for one vehicle, just steps from the front door - (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. PETS... This is not not a pet friendly home for weekly guests, however, monthly stays may bring a pet (a required $150 pet fee will be applied) that must be registered with the HOA prior to approval. CANCELLATION... Bookings 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. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! YOUR SLICE OF PARADISE IS CALLING...

OLD TOWN CUTIE CABANA… Bask in the charm of Old Town Key West as you approach this intimate and picturesque 2 bedroom townhome, located in the cozy enclave of Southernmost Cabana Community, just one block from famous Duval Street and the island's most popular spots. A rare find, this quaint getaway promises both proximity to all of the southernmost excitement yet tucked into a peaceful nest of serenity. Your perfect island retreat awaits you! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… A classic white picket fence greets you as you enter your tropical front yard and welcomes you to sit on your porch for a lovely cup of morning coffee and people watching. Ease into the entry where high ceilings and modern touches envelop you and open living and kitchen areas invite you to congregate with loved ones for entertaining and relaxation. Craft your favorite meals in the kitchen that boasts spacious countertops, stainless steel appliances and chef tools galore. Converse and dine at the breakfast bar for 3 or the cozy dining table for 4, then sprawl out on plush furnishings and enjoy a movie escape on your large wall-mounted TV. A full size washer/dryer closet and a full shower bathroom are located downstairs for your convenience. SLEEPING ARRANGEMENTS... Follow the stairs up to 2 plush king bedrooms that will tuck you in for an amazing night of slumber and rejuvenation. The primary bedroom offers an ensuite shower/tub combination and a private balcony for star-gazing and a nightcap. The guest bedroom features an ensuite shower bathroom. Both rooms are equipped with clothing dressers, storage closets and TVs for your enjoyment. OUTDOOR LIVING... Step outside to your spacious private back deck with ample and comfy seating and toss your fresh catch and steaks on the grill while sipping on a frosted cocktail. Enjoy the peace of listening to balmy breezes tickling swaying palms and the joyful sounds of nature in this ultimate serene setting. Follow the beautiful stone pathway that ambles throughout the cabana community and delights your senses with the grandeur of mature treescapes and lush gardens. You are only steps away from the gorgeous shared pool with a soothing waterfall feature. This home comes with 1 off street covered parking spot. PETS... This home does not allow pets. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This 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. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). SETTLE DOWN IN HEAVEN…

YOUR STORYBOOK COTTAGE... This island delight is tucked away on a vibrant and secluded street of The Meadows neighborhood. Your location is ideal for biking or walking to all of the sights and experiences that define Key West and make it a perfect island getaway. Throw your cares away as you approach this peaceful setting that promises tropical living at its best. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... This charming two-story cottage offers 3 bedrooms and 2.5 baths that will meet all of your creature comfort needs. Enter through your private white picket gated fence and let your vacation plans unfold on the cozy front porch as you sway on the swing with a cocktail in hand. As you enter the home, abundant natural light plays across the interior's vaulted ceilings while the modern and updated living and dining areas boast an outstanding space for entertaining loved ones. The dine in kitchen features stainless appliances, granite counters, a breakfast bar with seating for 3 and the gathering area is fully stocked to satisfy all of your cooking pleasures. The living area off the kitchen is an ideal spot for sinking down on plush seating while sipping on your chilled cocktail and feasting on your favorite tv shows. Slider doors merge your indoor with your outdoor living in classic Key West style. A powder room is situated just off the living area for your convenience. SLEEPING ARRANGEMENTS... There is a bedroom with a queen bed and en suite shower bathroom, dresser and hanging closet downstairs and a second guest room with a cozy twin bunk bed. Travel upstairs to a second primary king bedroom that welcomes you with expansive luxury. Enjoy your en suite bathroom with a shower, clothing dresser, hanging closet and a plush white couch for catching up with your favorite novel. A sofa sleeper accommodates additional sleeping arrangements. OUTDOOR LIVING... Enjoy your perfect front porch rocking chair seating for relaxing with your morning coffee . The newly landscaped lush backyard offers a private pool/spa and a whimsical outdoor shower. Enjoy dining in the evening breeze at your outdoor table and sink down into the plush outdoor furniture where you're surrounded by stunning tropical foliage and fairy lights. PARKING... This home does not have designated parking but there is generally available on-street parking directly in front of the home. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates. PETS... This property considers dogs up to 40 lbs. Please include the size and breed in the comments when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! BOOKING DATES... This home is only available as a monthly rental (28 night min). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). START YOUR ISLAND STORY HERE...

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

PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane in the desirable gated community of historic Truman Annex. Leave your worries on the mainland and step into this timeless neighborhood which is just steps from all the Key West fun. Cozy, spacious guest rooms, cheery island decor and lush tropical palm trees swaying all around have you feeling like you are truly in Paradise.  ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Pull up to your island dream home with off street parking and step inside this serene getaway. Enjoy an open floor plan with high ceilings, terra cotta tile floors throughout and incredible natural lighting seen through several sets of French doors looking out to the picturesque tropical pool area. Whip up your favorite meals with the family in the updated and fully equipped kitchen that comes with granite countertops and stainless steel appliances. Indoor seating for 6 and ample outdoor dining allow for enjoying your family meals together. SLEEPING ARRANGEMENTS... The first level comes with a guest room consisting of a queen size bed and en suite full bathroom. French doors from the guest room open up to the inviting outdoor pool space and seating area. Adjacent to the great room is a convenient half bath. Travel upstairs to find the master king suite that opens up to a private, covered balcony overlooking the lush pool area during your morning coffee or evening cocktail hour. Steps across the hall you will find another cozy king guest bedroom. All bedrooms come with ceiling fans, flat screen TVs and en suite bathrooms with a shower/tub combo. OUTDOOR LIVING... Wind down out on the covered back deck area with several loungers surrounding and a propane gas grill which make for the perfect family entertainment spot. The spacious heated private heated lap pool is the perfect evening activity to wrap up a fun Key West day by swimming under the stars in your peaceful surroundings. This community’s pathways are just a few steps away from all the island's main attractions including Fort Zachary Taylor State Park, Truman White House and all the best local bars, restaurants and tourist attractions. PARKING... Driveway fits up to two vehicles. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property. PETS... Pets are ONLY permitted for a month stay with a $400 pet fee. Please provide pet size, breed and age upon booking. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings 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. PREPARE FOR PARADISE...