33040, Florida, United States Vacation Rental Homes By Owner - Page 68

Welcome to Livin' On Key West Time Vacation Rental! This 2-bed 2-bath townhome is located in the prestigious Key West Golf Club. This unique property boasts a large private fenced-in backyard with a 19x10 in-ground concrete private heated pool with waterfall, perfect for enjoying the sunshine and cooling off. Additionally, it has three porches, including a large screened-in porch with a ceiling fan, outdoor TV which is ideal for relaxing and enjoying the tropical ambiance. To top it off, take time to enjoy the NEW outdoor shower!brbrThis beautiful home has all the amenities you love including a washer/dryer, gas/charcoal grill, FREE parking, fully stocked kitchen, and is pet friendly. WANT MORE brbrCheck out the Key West Golf Course community which provides 2 heated community pools, fitness center, access to the Rees Jones Championship Golf Course and beautiful walking paths. br

Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach

Key West, Florida, United States

Bed

Bath

6

Sleeps

$804.38

Concierge Realty is proud to present luxury villas at The Galleon Resort!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Saturdays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrOverlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends at the Tiki Bar, or relax in the swimming pool. The observation deck guarantees stunning views, sunrise to sunset, star gazing. Rent a boat for a private viewing of the Keys or take a jet ski for a spin right from the marina. Work up a sweat at the on site gym and afterwards, relax your body & mind in the sauna.brbrTwo-bedroom suites sleep up to six, and include a full kitchen, dining area, and decked out living area. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe second bedroom will have either a Queen size bed or two twin beds. brWe offer many activities on site at the Galleon Resort and Marina. From fishing charters to sunset cruises, snorkel adventures, boat and jet ski rentals, parasailing to live music.brbrA resort fee of approximately $75/week (subject to change) or $20/day (for stays shorter than one week) will be collected by the resort at time of check-inbr brThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!

Key West, Florida, United States

Bed

Bath

Sleeps

$154.57

SIMPLISTIC ELEGANCE...brEnjoy easy tropical living in this quiet refuge located within Old Town where you can roost and immerse yourself in island joy. A charming adult only hideaway located tucked in serene surroundings with the opportunity to fully live like a local! This one bedroom condo has been lovingly restored to envelop you in all its simple charm.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brCome unwind in this cozy layout on the first floor with delightful accents and vintage Dade County walls throughout. Large windows attract incredible natural lighting in this cheery space with comfortable furnishings and a flat screen TV for lazy afternoons. Perch the doors open to a light filled sunroom to get lost in your favorite novel. A fully equipped kitchen allows for all your meal prep and cocktail crafting.brbrSLEEPING ARRANGEMENTS…brA queen guest room features a comfy canopy bed and plush bedding with a TV for a perfect night's sleep. A very stylish en suite bathroom will wash your cares away which offers a shower. This unit also has its own private washer and dryer.brbrOUTDOOR LIVING…brA second entrance from the kitchen area takes you out to your outdoor tropical oasis. Steps away you will find a friendly community pool (not heated) with plenty of loungers to soak up the island rays and seating to dine al fresco. Park your bike on the side of the building and stroll in town to meet old friends and new. brbrPETS...brPets are not considered at this home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.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 have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrAUTHENTIC KEY WEST...

NEWTON'S NEST ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo w/ Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$223.68

This top-floor condominium features 3 bedrooms and 2 bathrooms, situated in the beautiful La Brisa Complex. It is conveniently located directly across the street from Smathers Beach and just a 10-minute bike ride from downtown Key West. The master suite includes a king-sized bed and an en-suite bathroom, while both guest bedrooms are equipped with queen-sized beds. For entertainment, there are Smart TVs in both the master bedroom and the living room. The dining area comfortably seats six, and the full-sized, fully equipped kitchen includes a washer and dryer for your convenience. La Brisa offers a peaceful atmosphere, overlooking the salt ponds. The unit comes with one designated parking space. Residents and guests can enjoy the lovely amenities of the community, which include a tennis court, BBQ grills for communal use, and a heated outdoor swimming pool.

Sea Haven Delight A delight in Key West Open March 2026 - Great

Key West, Florida, United States

Bed

Bath

Sleeps

$175.08

Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticbrbrExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony overlooking a serene nature preserve—offering a quiet, tranquil setting within the property.brbrThe spacious master suite boasts a large walk-in closet and a stunning, custom-designed bathroom with a walk-in shower. The full-size, fully equipped kitchen makes dining in easy, and a full-size washer and dryer add convenience. Ample storage throughout the unit ensures a clutter-free stay.brbrLocated just across from the elevator, this unit offers easy access and includes one assigned covered parking space in a secure garage.brbrResort-Style Amenities Include:brbr Olympic-sized heated poolbr 20-person jacuzzibr Three tennis courts (including a clay court)br Small fitness centerbr Lush tropical landscaping and a peaceful settingbrbrThis is island living at its best—perfect for a relaxing vacation or an extended stay in Key West.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Come escape to Island Time Hideaway - Wonderful monthly renovated rental

Key West, Florida, United States

Bed

Bath

Sleeps

$1004.89

FAR FROM ORDINARY...brExtraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak in an alternate reality full of sunshine and serenity. Nestled just 1 block off the fun-loving Duval St., this cozy retreat makes your time in Paradise hard to leave with everything at your fingertips such as all the highly adored restaurants, bars and attractions. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brGreeted by swaying palms and lush greenery surrounding this charming tropical getaway, the stress of the real world instantly washes away. A front porch begins your time calling for a good book as you unwind and watch neighbors passing by. Find a bright and open Great Room inside outfitted with comfortable furnishings, a writing desk and a flat screen TV. A fully equipped kitchen area includes a table for 4 and bar top seating for 3. brbrSLEEPING ARRANGEMENTS...brFollow the stairs up to two comfortable guest rooms lying beyond charming barn doors for your peaceful night's rest. The first room comes with a queen bed and a TV with direct access to the front balcony with a charming swing to overlook the vibrant neighborhood. The second room comes with a king bed and a TV , as well as access to a rear facing private sundeck with loungers for your lazy days. Full bathroom with shower is located on the second floor. An additional half bathroom lies outside off the back porch area.brbrOUTDOOR LIVING...brSlip outside from the kitchen area to your covered, tranquil outdoor oasis. Grill up your fresh catch of the day to be enjoyed at the outdoor table for 4. Enjoy an outdoor shower so you can rinse off after a fun summer day out on the town. This property is just a stone's throw from the famous Duval St. making your time in Paradise practically perfect. brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 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.brbrPARADISE AT YOUR FINGERTIPS...

SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!

Key West, Florida, United States

Bed

Bath

Sleeps

$287.73

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king, 1 queen, sofa sleeper recommended for children ONLY)brBathrooms: 2 brLocation: Sunrise SuitesbrSquare Feet: 798brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, shared pool, close to beaches, private balconybrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Sunrise 307-2BR/2BA condo near beaches with pool, parking, balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$979.71

OVERVIEWbrThe Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as having “an open, crisp, private space”. The house has two (2) gabled ceilings, which creates a contemporary, spacious living environment. The downstairs floor is Golden Oak Pergo. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. brbrThe house has a Starlink high speed Wi-Fi network, streaming internet tv, a 43 Samsung SMART HDTV, and two (2) 26 Samsung SMART HDTVs. The house has central air conditioning, a ceiling fan, and access to a stacked washer and dryer. There is a stainless steel propane barbecue located on the pool deck. brbrThe house can comfortably accommodate a maximum of six (6) guests - who are comfortable sharing an open living environment.brbrFIRST FLOORbrThe kitchen, dining, living, and bathroom are located on the first floor. An architectural beam containing LED lighting extends the entire length of the house. The bathroom, located off the living room, is completely new and has recessed LED lighting, a full shower, and a pedestal sink. There are two (2) sets of French doors providing access to the rear courtyard where the 8'x10' heated Jacuzzi is located.brbrKITCHENbrThe contemporary galley kitchen is new with maple cabinets, black Zimbabwe granite counter tops, stainless steel single compartment sink, and the ceiling has recessed LED lighting. Kitchen equipment includes an under the counter GE refrigerator, an under the counter Sub-Zero freezer with ice maker, a stainless steel gas range, garbage disposal, Samsung microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and basic cooking utensils.brbrDINING ROOMbrThe dining room has a wood Parson's dining room table with seating for six (6), and a maple with black Zimbabwe granite service credenza - complete with wine rack.brbrLIVING ROOMbrThe living room has a queen sleeper sofa, a queen bed, a relaxing chair, a 43 Samsung SMART HDTV, and an Onkyo receiver.brbrMASTER LOFTbrA stair case is used to access the master loft sleeping area. The loft has a queen size bed and a 26 Samsung SMART HDTV.brbrGUEST LOFTbrA staircase is used to access the guest loft sleeping area. The loft has a full size bed and a 26 Samsung SMART HDTV.brbrAll linens and towels are furnished.brbrCOMMON ELEMENTSbrThe five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is a Starlink secured wireless wifi network, and CCTV security monitoring. The design of the property lends itself perfectly for small gatherings with friends and family.brbrLANDSCAPINGbrThe landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways. brbrEXCELLENT LOCATIONbrThe house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the center of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.brbrCHICKENS & ROOSTERSbrThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!brbrCRITTERSbrAlso, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.

Historic Old Town Key West - Turtle House, Sleeps 6

Key West, Florida, United States

Bed

1

Bath

5

Sleeps

$457.01

brGive me a call if you have any questions!br702-232-3750. Welcome to your home away from home and enter through the canopy of trees to the secure, patrolled Shipyard Condominium's in the desirable Truman Annex Complex. Professionally designed to maximize relaxation and encourage adventure. BeautifulbrRelax on the balcony with your glass of wine or hang out on the reading porch with a cup of coffee and a great book. Fort Zachary Taylor State Beach is a 2 minute bike ride away. This wonderful home has been newly decorated with a conch farm theme, comfortable outdoor furniture, professionally designed bedrooms with new queen beds in each room , fully stocked kitchen, living room, washer/dryer. Some of the amenities include WIFI, SMART TV's, and an assigned parking spot . Steps from the world famous Duval Street, sunset celebration and all the downtown action one desires. You are only one block down from The Green Parrot, rated the 3rd best bar in America. The Shipyard is the closest residential location to Fort Zachary State Park and Beach. You are in the heart of Old Town, Mallory Square (sunset celebration) and on the grounds of Harry Truman's Little White House located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are landscaped with 30’ palms and exotic flowering plants. It is just a short stroll to the Historic “Little White House” where President Truman called home whenever he could. You are close by the warm tropical waters of the Gulf of Mexico where you can hop on a fishing boat for flats or deep sea fishing, take the Ferry to Sunset Key for lunch or dinner, go parasailing, snorkeling, diving, shopping, dining or wherever your dreams might take you. Just another short stroll takes you to Mallory Square where the world renowned “Sunset Celebration” occurs every day! This event is a “don’t miss” of things to do in Key West.brbrWe provide all of your kitchen necessities, just bring the cook & the food! Spacious living room where the living room doors open up into the private deck making your vacation a true Tropical experience. brbrWhat is provided:brbrWe provide 4 towels, wash cloths for each reservation as well as 2 bath robes and beach towels.brbrWe provide 2 rolls of toilet paper and 1 roll of paper towels per reservation. Please bring extra if this is not enough.brbrDaily maid service is not provided.

Key West Hen

Key West, Florida, United States

Bed

Bath

Sleeps

$345.71

Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach, a low key paradise has a beautiful open layout, with views of the large private patio and heated pool visible as soon as you enter. Guests can walk to nearby higgs beach, and higgs beach dog park— perfect for your family member with fur! (dogs are welcome.) the hustle and bustle of duval street is just a quick 15 minute walk, or 5 minute bike ride away as well.brbrThroughout the house, you will find brand new, high-end tiles and crown molding, as well as brand new paint. brThe master bedroom has a fully-renovated en suite bathroom that includes double vanity sinks, a luxury shower with ceiling-mounted rainfall shower head, a riverstone shower floor, tiled shower bench, a brand new toilet, brand new rubbed bronze fixtures and floor to ceiling tile. Additional amenities in the master bedroom include 47 inch wall-mounted hd tv and french doors leading out to the gorgeous patio and pool area. The second bedroom has a queen bed, full futon, hd tv, brand new, full, plush carpeting, and is next to the newly-renovated second bathroom with floor to ceiling upgraded tile, new vanity and sink, new toilet and new brushed nickle bathroom fixtures. A second large sitting area also has a full pull-out couch for more sleeping options. Enjoy the comfortable new living room furniture while reading a good book, or watching your favorite show on the 60 inch hd tv. Or if you want to enjoy the beautiful key west weather, head outside to your private patio and pool area, and relax by the pool, or sit at your private bar and watch the big game on your private outdoor hd tv, while surrounded by mature, colorful, tropical landscaping. brbrAdditional amenities include wifi all-in-one printer/scanner/copier, and a porch swing and rocking chair on front patio. brbrCANCELLATION POLICY: Although we do not guarantee refunds for cancellations; in the past we have had a few guests' need/want to cancel their reservations for various reasons. We immediately relisted our house as available on VRBO and successfully rebooked the vacation dates every time-- making it possible for us to refund the original guest their deposit(s). While not a guaranteed return of money-- it has worked in the past!brbrbrbr

**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach

Key West, Florida, United States

Bed

Bath

8

Sleeps

$414.46

Summary:brbrLuxury 4bdr/4ba house with pool&dockbrbrbrbrThe Space:brbrIf you're looking for a luxurious and unforgettable waterfront vacation experience, look no further than this stunning vacation rental property on the Key Haven Peninsula. Surrounded by water on three sides, this property boasts an impressive 245 feet of canal frontage with two boat lifts, a double car garage, and a beautiful pool for your enjoyment. The 15000 square foot lot is surrounded by magnificent tropical gardens, creating a breathtaking and tranquil setting for your stay. Inside, you'll find over 3000 square feet of living space, with fine interior design and amenities that exude comfort and luxury. The large kitchen is fully equipped with modern appliances and ample counter space, making it easy to prepare meals for your family and friends. The spacious living and dining areas provide plenty of room for entertaining guests and hosting dinner parties. This property features 4 perfectly scaled bedrooms, each with its own private bathroom. The bedrooms are designed with luxury and comfort in mind, providing a peaceful retreat for guests after a long day spent on the water. The high-quality amenities and attention to detail throughout the property ensure that your stay is comfortable, enjoyable, and unforgettable. Whether you're a seasoned boater or just looking for a waterfront getaway, this vacation rental property is the perfect choice for your next vacation. You'll have everything you need for the ultimate waterfront vacation experience, from the beautiful pool to the stunning tropical gardens. This spacious and high-quality home is perfect for families, groups of friends, or anyone looking for a luxurious and relaxing getaway. Book your stay now at this stunning vacation rental property and experience the ultimate waterfront Key West vacation.

Triple Crown Villa- Boaters paradise with Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$284.29

PERFECT CAREFREE RETREAT...brLocated in the small private community of Porter Court within Truman Annex and set around a graceful pool and hot tub. This is a smaller community within the gated Truman Annex community that provides a little extra privacy and peace and quiet. This delightful 2 bedroom 2.5 bath townhome is mere steps from all the excitement and beauty that is Key West. This highly coveted community is within walking distance of the famous Duval Street, Mallory Square, world-famous sunsets and countless restaurants and galleries. This prime location places you close to all the fun and attractions but is a quiet and peaceful refuge for your island bliss.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter through the front gate where you are greeted by a cozy porch that entices you to sit and enjoy cool island breezes while you plan your island adventures. Enter through the front door to the open kitchen and living areas that have been lovingly updated and maintained. Fashion your foodie favorites in the fully-equipped kitchen which includes an electric stove, microwave, large French door refrigerator, coffee maker, toaster oven, and kitchen breakfast bar area (seats 2). The cabinets house every tool and appliance you will need to whip up scrumptious meals. Gather around the dining table for 6, then settle down on the plush sectional couch (also converts to sleeper sofa) and enjoy your favorite programs on the large wall-mounted TV. A powder room is located in the living area.brbrSLEEPING ARRANGEMENTS...brTravel up the stairs to two en-suite guest rooms when you're ready to rest and refresh for the next day's adventures. The first bedroom features two twin beds that can convert to a king upon request, a desk/work area, large double closets, a smart TV and large windows that allow plenty of cheerful sunshine inside. The bathroom offers a shower/tub combination. The second bedroom also features a king bed, double closets with built-in storage, smart TV, and a charming balcony with seating for two that has a view of the community pool and gardens. The en suite bathroom offers a tiled rain shower. A laundry closet is located upstairs and features a full-size stacked washer and dryer.brbrOUTDOOR LIVING...brFrench doors open to a lovely private deck area with deluxe outdoor furnishings and lush foliage. Fire up the grill and dine al fresco under the sultry tropical stars. Swimming in the semi-private heated pool and spa is a great way to wash off the day and it's just steps from the home. This unit is uniquely situated around the pool/spa for easy access and is shared by a smaller number of units compared to the busier pools in Truman Annex. There is also a cabana with restrooms in the pool area and ample lounging chairs for your sunbathing pleasure.brbrPARKING.... brThis home does offer parking for one vehicle, but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. The maximum length of the vehicle is 18 feet.brbrPETS...brThis is not a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrCONCIERGE SERVICES...brEnjoy 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!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.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).

SALTWATER REMEDY~2BR/2.5Ba Truman Annex/Porter Crt Townhome/Semi-private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$299.45

IN THE HEART OF IT ALL…brA perfect location within a peaceful setting, this updated home allows for extraordinary moments as you truly immerse yourself in island life. A lush backdrop to this highly coveted neighborhood, this home welcomes you inside to cozy surroundings creating memories that will last for a lifetime.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brStep inside to an open and cherry space boasting soaring ceilings and plentiful space for your family gatherings. Enjoy prepping meals together in this fully equipped kitchen with bar seating for 4 and indoor dining for 4. Comfortable furnishings surround the living space with a TV for lazy days with lush views of your outdoor oasis through a set of French doors.brbrSLEEPING ARRANGEMENTS…brFind a plush queen primary suite up the stairs equipped with a TV and an en suite bathroom with a shower/tub combination with a private balcony surrounded by vibrant vegetation. The 3rd floor comes with a 2nd queen guest room with a TV and en suite bathroom with a shower. A sofa sleeper resides in the living room with convenience to a powder room off the kitchen.brbrOUTDOOR LIVING… brEnjoy your very own slice of Paradise on your private deck and patio as your grill up your fresh catch over Happy Hour. Cool off in the Foundry community pool equipped with plenty of loungers. Located in the most desirable community in Key West, this home is walking distance from the Truman Waterfront, Truman Little White House and all the fun on Duval St. brbrPETS...brPets 10 pounds or less are allowed with a required pet fee. Please include the size and breed when inquiring.brbrPARKING...brA parking spot is available to you to make coming and going a breeze! No trailers, boats, jet skis or motor homes are allowed. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrbrBOOKING 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. 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.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCOME LIVE ON ISLAND TIME…

TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!

Key West, Florida, United States

Bed

Bath

Sleeps

$193.08

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCUTE CONDO IN STEPS FROM IT ALL…brThis 2 bedroom, 1 bath ground level flat is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This cozy downstairs unit has everything you'll need for your stay in paradise!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter through the white picket fence and you are greeted by a lovely front porch with sitting area where you can sip coffee and plan your island adventures for the day. The flowing floor plan offers a spacious and lovely living and dining area that offer rest and relaxation after a day in the sultry sun and balmy breezes of the island. Whip up your favorite recipes in the fully equipped and stocked kitchen that overlooks the living area. A dining table for 4 sits next to the kitchen where you can enjoy cozy meals with your loved ones. A comfy couch, plush cushioned chairs and smart tv in the living area provide the perfect resting spot for bingeing on your latest shows and movies. A stacked laundry closet sits just off the living area for your convenience. Open the French Doors to your sweet backyard oasis.brbrSLEEPING ARRANGEMENTS…brThe first queen bedroom is on the left as you enter the home. It offers a spacious hanging closet, smart tv, and a clothing dresser for your belongings. The primary bedroom also has a queen bed, smart tv, large hanging closet and clothing dresser, and is adjacent to the full bathroom, where you can wash off the day in the shower/tub combination. brbrOUTDOOR LIVING…brThe Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door in the living area to the delightful private deck, a shaded retreat outfitted for unwinding and refreshment.br brPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. 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. 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.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrYOUR SWEET RETREAT...

THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$855.56

Experience true tropical Key West living as the locals do in this spacious mid-century private garden oasis home with large swimming pool and poolside entertainment cabana. Located just one block from the beach, Private Pool Garden Villa vacation rental is at once exotic and comfortable. The colorful interior walls with French doors and windows throughout the house become picture frames anchoring the lush tropical garden that surrounds the property.brbrAuthentic tropical style is what this corner lot property offers. A variety of lush foliage peaks over the high lattice topped fence. Bright red blooming bougainvillea vines drape the trellis entrance and then a bricked pathway inside the gate winds its way through the garden and leads to the front door. A variety of mature palm trees provide a rich calm feeling. Beautiful landscape lighting creates an enchanted feeling at night.brbrInside the Private Pool Garden home, the spacious open living room/kitchen floor plan, is made to feel even larger with expansive vaulted ceilings and brightly colored walls. An extensive renovation of this mid-century ranch style house was completed in the 1970`s to create the beautiful pool, cabana, lush garden, and spacious open living room kitchen floor plan. Now considered `vintage modern` the authentic 70`s design is complete with a white painted brick fire place. French doors open to the focal point of this unique home that is most definitely the large salt water swimming pool, complete with poolside cabana and extensive garden.brbrThe floor plan of this home is traditional with all three bedrooms located off the hall that leads from the main living area. This home provides two master bedrooms - one bedroom with a king size bed, one with a queen size bed, both have en-suite bathroom. A unique added feature is a bricked courtyard outside the blue master bedroom and little intriguing garden space for relaxation. The other Master, paneled in classic Dade County Pine, features a solarium which practically brings the outdoors inside.brbrThe third (spare) bedroom, also off the hall, is cozy and has a tropical forest view of the garden. Bedding is a trundle bed that offers one or two twins. The half bath (i.e. sink and toilet) are directly across the hall from the third bedroom.brbrBedding Summary:brbr1 king size bed, 1 Queen size bed, and a trundle bed (2 twins).brbrSpecial Features: Very large salt water swimming pool (a Key West rarity,) and fun outdoor cabana entertaining area; Close to the beach.brbrAmenities: Large swimming pool (heat optional) with large garden, fenced yard, full kitchen, A/C, W/D, color cable TV, BBQ grill, C/D player and stereo. Linens and towels provided, easy neighborhood parking next to house. Pets allowed, restrictions apply.brbrArea: The property is very unique for a Key West weekly rental in that it is located in a quiet residential area away from most vacation rentals that are licensed to rent weekly. Situated on corner lot, there are neighbors only on one side. There is plenty of room to lounge at the pool in the large garden area.Located on the south side of the island in the beachside neighborhood, the houses on this street are less than a five minute walk to Higgs Memorial Beach. It`s not unusual to see folks walking or biking to the beach in their bathing suits with towel and cooler under arm. Enjoy the paved biking and walking path stretches along the beaches, beach volleyball, tennis, pickleball and bocce. Famous laid back Salute Restaurant on the Beach has great food and a full bar. The Civil war fort, West Martello Tower is the home of the Key West Garden Club, a gorgeous place to visit, and a beautiful place to stage a beach wedding.brbrActivities: Beach, shopping, restaurants, museums, sailing, boating, snorkeling, diving, theatre, night life, family activities. Close access to Old Town.brbrRestrictions: The property will not tolerate smoking inside. The property is located in a residential neighborhood and is definitely not suitable for staging loud parties. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Key West Private Pool Garden Villa - 2 Blocks from Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$466.88

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes:brbr2 bedrooms 2 full bath {queen and king bedrooms} plus a sleeper sofa in the living room.brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brSecond floor condo with outdoor balcony.brLarge shared Shipyard pool located just steps away.br3 Smart TV's and Amazon Echo (just tell Alexa to play some Jimmy Buffett!)brHigh speed fiber optic internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.

Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!

Key West, Florida, United States

Bed

Bath

5

Sleeps

$216.29

Welcome to one of the most sought-after neighborhoods in Key West—Truman Annex. This quiet, gated community is known for its beautifully manicured grounds, tropical ambiance, 24/7 security, and unbeatable walkability. Just outside the gates, you’ll find yourself within minutes of everything Old Town has to offer. Duval Street’s vibrant nightlife, Mallory Square’s famous sunsets, and several of the island’s best beaches are all just a short walk or bike ride away. Whether you’re here to explore or simply unwind, the location offers the perfect mix of accessibility and escape—close enough to enjoy the excitement of the island at a moment’s notice, yet tucked away in a private, secure setting where you can relax and recharge. brDesigned for effortless island living, this inviting condo is equipped with everything you need to relax and feel at home. Start your morning sipping coffee or tea on the covered deck, surrounded by swaying palms and warm breezes, or cool off in the community pool after a day in the sun. Two bikes are included and securely stored just outside your door, making it easy to explore the island at your own pace. Prefer to drive A reserved parking spot is provided for your convenience. brFor beach outings, you’ll have access to beach chairs, towels, sunscreen, snorkels and masks, water shoes, and beach bags—everything you need for a carefree day to make the most of the crystal-clear waters. Inside, the fully stocked kitchen offers all the essentials for cooking if you choose to dine in. With a mix of practical comforts and coastal charm, this peaceful retreat provides the ideal space to unwind, explore, and enjoy the best of Key West—offering a more personal experience with added privacy, space, and local flavor than a typical hotel stay.brGuests have exclusive use of the second floor condo and can gain access by use of a lockbox. This condo is located on the second floor. Please note the step into the shower is 19”.

Apartment

Southard Quarter at Truman Annex | Walk to Duval

Key West, Florida, United States

1

Bed

1

Bath

3

Sleeps

$560.59

Imagine stepping into your own slice of paradise at the Belle of Old Town in the heart of Key West. This stunning four-bedroom, four-bathroom vacation rental offers an unparalleled blend of comfort, luxury, and vibrant island charm.brbrUpon entering, you're greeted by an open-concept living space that seamlessly flows into a gourmet kitchen, complete with modern appliances and a spacious dining area. The sleek, contemporary design is punctuated by warm, inviting touches that make you feel right at home.brbrEach bedroom boasts plush bedding, en-suite bathrooms, and ample closet space, ensuring a restful night's sleep for all guests. The master suite is a true haven, featuring a king-sized bed, a walk-in closet, and a private balcony. Additional amenities include a private heated pool, perfect for cooling off during the hot Florida days, and a spacious deck with a built-in grill, ideal for evening barbecues under the stars.brbrKey West offers an array of adventures just steps from your door. Dive into marine life at the Key West Aquarium, explore the historic streets of the Key West Historic Seaport, or catch the famous Sunset Celebration at Mallory Square. For nature enthusiasts, the Key West Butterfly and Nature Conservatory is a must-visit, while outdoor enthusiasts will love the opportunities for snorkeling, kayaking, and dolphin watching right in the surrounding waters.brbrWhether you're seeking relaxation or adventure, Belle of Old Town provides the perfect base for your Key West getaway. Book your stay today and immerse yourself in the vibrant lifestyle of this tropical paradise.brbrAccommodations:br** Bedroom #1: first floor, king bedbr** Main bedrooom: second floor, king bed, large ensite bath, with large walk in shower.br** Bedroom #3: second floor, king bedbr** Bedroom #4 - Off the pool, king bed, private bath.brbrOther rental information:br** This property has off street parking. br** Minimum 29 night staybr** Available for rentals April - November only

New Property - Belle of Key West! Old Town 29 nt min.

Key West, Florida, United States

Bed

Bath

Sleeps

$958.67