Home Vacation Home Rentals By Owner In Key West, FL

Showing 360 Of 878 Vacation Rentals
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Exceptional(15)

$303.9

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Private Vacation Home

Road's End | Prime Old Town Location! Updated Home w/ Pool

Key West, Florida, United States

Road's EndbrbrStep into Road's End, your inviting retreat just steps from Duval Street, where the charm of Old Town Key West meets peaceful garden living—perfect for travelers seeking a relaxing escape in the heart of the island.brbrThe Space:brRoad's End offers a welcoming two-level layout designed for comfort and convenience. The lower level features a cozy living area with a queen sleeper sofa for additional guests, a convenient half bath, and a fully equipped kitchen with modern appliances for easy at-home dining. Upstairs, the spacious king bedroom provides an inviting escape complete with a dedicated workspace, ample storage, and a full ensuite bathroom. With natural light, tasteful coastal décor, and all the essentials for a relaxing stay, this townhome delivers a warm and comfortable home base for your Key West adventure.brbrGuest Perks:brTake advantage of easy contactless check-in with a personalized access code provided before arrival. Guests also enjoy shared access to a beautifully landscaped courtyard featuring a heated outdoor plunge pool, onsite laundry, and peaceful outdoor seating areas perfect for enjoying the island breeze.brbrNeighborhood Highlights:brPerfectly situated just off the southern end of Duval Street, Road's End places you within walking distance of the Southernmost Point, the Hemingway Home, the Key West Lighthouse, and beloved local restaurants including Blue Heaven, Moondog Café, Rams Head Southernmost, and Better Than Sex Dessert Restaurant. From charming cafés to iconic landmarks, everything Old Town has to offer is just moments away.brbrGetting Around:brExplore the island with ease—walk to many nearby attractions, or rent a bike, scooter, moke, or golf cart for added convenience. Rideshares, taxis, and pedi-cabs are also readily available. Street parking is available in the area on a first-come, first-served basis.brbrOther Things to Note:br- Pet-Friendly! Up to 2 dogs (40lbs maximum) with a $20 per pet per night fee.br- Onsite shared washer/dryer in unit.br- Shared heated plunge pool located in the courtyard.br- Guests must be 25 years of age or older to reserve this property.br- The primary bedroom is located on the second floorbrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt 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.brbrTo promote guest safety, exterior security cameras are in place around common outdoor areas including pathways, entrances, and the courtyard. No cameras are located inside the home or in private spaces.
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Bath 1

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Sleep 4

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Exceptional(25)

$490.45

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Private Vacation Home

A Caribbean Alternative townhome in Truman Annex

Key West, Florida, United States

A Caribbean Alternative is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West.  This townhome provides convenient access to all the exciting activities and world-class eateries and bars offered in downtown Key West. We encourage you to leave your car at home and enjoy walking, biking, or scootering to almost anywhere you want to go.brbrThis lovely 2 bedroom, 2 1/2 bath townhome is nicely appointed with stainless steel appliances, a washer and dryer, and a covered outdoor seating area. The living area has homey seating with a flat screen television and Bose sound system. The French doors open up onto the covered deck and cleanly landscaped yard. brbrUpstairs are two bedrooms, both with ensuite bathrooms, queen beds, and ample closet space. Both bedrooms open to a covered porch with relaxed seating options. A washer and dryer are located in the hallway between the 2 bedrooms for your convenience. brbrThe Truman Annex Waterfront Park is close by with walking paths, open areas to play or relax, and a splash pad and park for the kids to play. Fort Zachary Taylor State Park and Beach are also close by and offer picnic areas with grills, as well as beach areas that are ideal for snorkeling and sunbathing. There are chairs and umbrellas for rent as well as a full concession stand and restrooms.brbrEnjoy the quaintness of this peaceful neighborhood on your next visit to Key West and be close to all there is to do on our beautiful island. brbrThis is a weekly rental.  brbrOnly one parking space is provided for this unit -parking can be difficult - no trucks/campers or oversized vehicles.brbrSorry, no pets allowed per the HOA
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Bath 2

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Sleep 4

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$615.63

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Private Vacation Home

Atlantic Cabana | Luxury 3-Bedroom Townhome Steps

Key West, Florida, United States

Atlantic Cabana | Luxury 3-Bedroom Townhome Steps from the OceanbrbrEscape to the beauty and tranquility of Key West at Atlantic Cabana, a stunning 3-bedroom, 3-bathroom townhome offering 1,950 sq. ft. of contemporary living space. Built in 2007, this stylish corner townhome features top-of-the-line finishes and a prime location just steps from the Atlantic Ocean, pristine beaches, and nearby attractions. Whether you're soaking up the sun at the beach or relaxing in your private pool, Atlantic Cabana is the perfect destination for an unforgettable island getaway.brbrThe Ambiance:brFrom the moment you step inside, you'll be greeted by an open-concept design, filled with natural light and modern touches. The spacious layout is perfect for both family vacations and group gatherings, with ample room for everyone to unwind and enjoy. High-end materials such as stainless steel appliances, granite countertops, and hardwood floors elevate the home's chic, beachy vibe, while the private pool and deck area invite you to enjoy the outdoors in complete privacy.brbrHighlights include:br- A fully equipped kitchen with stainless steel appliances and a large kitchen island ideal for preparing meals and entertainingbr- A private, heated pool and outdoor deck perfect for relaxing or hosting friends and familybr- Three beautifully appointed bedrooms, including two king-sized beds and a queen-sized bedbr- Three bathrooms featuring modern finishes, with two en-suite and one shared bathbr- Shaded balconies off each upstairs bedroom with peaceful views of the neighborhood and the poolbrbrGuest Access:brAtlantic Cabana offers complete convenience with private off-street parking, including space for two cars in the driveway, plus free street parking available at all times. The townhome is fully furnished, and a stackable washer and dryer is located on the second floor for your ease. We also provide detergent and dryer sheets to get you started, so you can pack light and focus on enjoying your vacation.brbrLocation Highlights:brNestled in the quiet Mid Town area of Key West, Atlantic Cabana is located just a few blocks from Higgs Beach and the White Street Pier. Nearby you'll find the Indigenous Park, a popular dog park, and a variety of outdoor activities including volleyball and pickleball courts. Whether you're biking or driving, you're just a short 5-minute drive or 10-minute bike ride from the iconic Duval Street, where you can explore the island's lively nightlife, world-class restaurants, and unique shops.brbrTransportation Tips:brGetting around Key West is a breeze from Atlantic Cabana. With private parking for up to two cars, you can easily explore the island by car or bike. For further convenience, there are also taxis and rideshare options available, as well as public transportation to help you explore all that Key West has to offer.brbrOther Things to Note:br- Central air conditioning for ultimate comfort during your staybr- On-site off-street parking for your conveniencebr- Washer and dryer available for guest usebr- Mid-stay cleaning available upon requestbr- A minimum stay of 30 days is required, in accordance with local regulations.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrAt Colocada Vacation Rentals, we are dedicated to providing a luxurious and memorable Key West experience. If you have any questions or need assistance during your stay, our friendly local team is available to ensure your vacation is everything you dreamed of and more!
Bed 3

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Bath 3

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Sleep 6

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$366.25

/ Nightly
Private Vacation Home

Starfish Oasis at Casa Marina, 2BR - Heated Pool - Hot Tub - 2 Parking - Pets OK

Key West, Florida, United States

Starfish Oasis at Casa Marina offers 2BR, heated & chilled pool, hot tub, private parking for 2 large vehicles, pet-friendly, and just an 8-minute walk to the beach.brbrThis home is only available as a MONTHLY RENTAL with 28 NIGHT MINIMUM. Booking is by the calendar month (first day of the month to the last). Alternate dates may be considered if the calendar/occupancy allows.brbrStarfish Oasis at Casa Marina – Garden-Level Poolside Retreat is a tropical paradise located in one of Key West’s most coveted residential neighborhoods. This completely renovated duplex home offers the entire private downstairs residence with two bedrooms, two full bathrooms, a spacious open-concept living area, and a fully equipped kitchen—ideal for couples, friends, or small families seeking an authentic island escape.brStep outside to a lush shared tropical outdoor space featuring a one-of-a-kind sailboat cocktail swimming pool, hot tub, outdoor bar with TV, and a commercial outdoor chef’s kitchen designed for relaxed evenings and effortless island living. Comfortable seating areas and a large two-person hammock create inviting places to unwind beneath the palms.brbrThe Space:brThe Garden-Level Poolside Retreat is thoughtfully designed for comfortable extended stays, easygoing Key West living, quality time, and relaxed entertaining.brThe open living area reflects authentic Key West style, perfect for reading, relaxing, or planning your next adventure. A dedicated work nook offers a quiet and comfortable spot for remote work or trip planning.brThe primary bedroom features a private en suite bathroom, while the second bedroom is located adjacent to a second full bathroom, providing privacy and comfort for all guests. Both bedrooms offer excellent sleep quality and feature separate exterior entrances, making it easy to step out for an evening soak in the hot tub.brThe fully equipped indoor kitchen includes all the essentials for everyday cooking, while the commercial outdoor kitchen is a true chef’s delight for effortless island dining. A Weber grill, Traeger smoker, and Big Green Egg create an exceptional setup for outdoor cooking enthusiasts.brFull-size, in-unit laundry facilities are provided exclusively for guest use.brEvery detail blends modern comfort with tropical charm, creating an inviting atmosphere that encourages guests to slow down, settle in, and live like locals. High-speed internet and keyless entry ensure a seamless and convenient stay.brbrGuest Access:brGuests enjoy exclusive access to the entire downstairs residence, including the bedrooms, bathrooms, living area, kitchen, and laundry facilities.brThe outdoor space is shared only with the upstairs residence and is never open to the public, allowing guests to fully relax and enjoy a private, resort-style setting.brSelf check-in is simple and seamless with a personalized access code prior to arrival, along with direct contact information for the local owner/manager, who may be in residence onsite occasionally but respects your privacy at all times. Host is available for questions, assistance, or local recommendations throughout the stay. brbrThe Neighborhood:brCasa Marina is one of Key West’s most desirable residential neighborhoods, known for its understated elegance, historic island homes, and close proximity to beaches and Old Town. Guests enjoy quiet, palm-lined streets and a refined, peaceful setting that makes it easy to experience the island like a local—returning each day to a calm, comfortable retreat away from the crowds.brbrExplore & Dine Nearby:brEnjoy sunrise or sunset walks to White Street Pier or the Southernmost Point. Higgs Beach is just a short distance away and offers chair and umbrella rentals, kayaks, and stand-up paddleboards. Nearby amenities include bocce ball courts, tennis, pickleball, and volleyball courts, as well as a dog park and children’s playground. Explore the historic West Martello Tower and botanical gardens, or enjoy local dining favorites such as Louie’s Backyard, Salute! on the Beach, and White Street Pizza.brGuests are always welcome to ask their local host for personalized recommendations and insider tips to truly live like a local.brbrGetting Around:brThe driveway provides parking for up to full-sized two vehicles. Golf carts, scooters, and bicycles are popular and convenient ways to explore the island, and Uber service is readily available.brbrOther Things to Note:brDogs are welcome with PRIOR approval only. A maximum of two dogs is permitted. A $250 pet fee per stay applies. Dogs must be well-behaved, house-trained, and not disturb neighbors. Guests are responsible for all cleanup inside and outside the property. Some breed restrictions apply. Failure to disclose pets may result in additional fees or cancellation.
Bed 2

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Bath 2

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Sleep 4

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Exceptional(16)

$205.57

/ Nightly
Private Vacation Home

BELLA VITA ~ 2/1.5 located in the Truman Annex with a community pool!

Key West, Florida, United States

IDEAL LOCATION IN GREAT COMMUNITY...brEnjoy your stay at the President's Walk at Truman Annex.  This well manicured community is set in a wonderful location which is walking distance to most that Key West offers! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS...brThe first floor includes a living room, dining area, fully equipped kitchen and a half bath.  The sitting area has a comfortable sofa and coffee table situated to view out of the 2 sets of French doors.  The dining table is centrally located for meals, playing cards or just enjoying each others company.brbrSLEEPING ARRANGEMENTS...brThe second floor is outfitted with two bedrooms.  The master bedroom has a comfortable queen size bed, a closet for hanging, dresser for storage and a French door which leads out to a small deck with seating.  There is Roku TV available only in the master(downstairs has cable). There is also a half bath with a toilet and sink en suite.  The guest room has a queen size bed, a large closet and a door leading to a deck.  In the upstairs hall you will find the full bathroom.  There is a large double vanity and a shower with enclosure. brbrPOOL AND OUTDOOR LIVING...brOpen the French doors and step onto the patio to relax. There is a grill ready to cook your fresh catch so you can dine outside under the stars. The heated community pool is just a short walk from the home and this Old Town location is conveniently situated near Duval Street, waterfront sunsets at Mallory Square and locals favorite beach at Fort Zachary Taylor.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)brbrPARKING...brThis home comes with an assigned parking space. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.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).brbrNO TIME LIKE ISLAND TIME...
Bed 2

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Bath 1

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Sleep 4

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$858.0

/ Nightly
Private Vacation Home

Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath

Key West, Florida, United States

Looking for the perfect spot to soak up some sunshine and unwind in Key West You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one).brbrStep inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun.brbrThe living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring.brbrBoth bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together.brbrOutside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise.brbrIsland Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great memories.brbrP.S. The pool is all yours—no sharing here! Pool heat available when requested. brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
Bed 2

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Bath 2

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Sleep 4

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Exceptional(5)

$362.17

/ Nightly
Private Vacation Home

~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!

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 home via its white picket fence and comfortable front porch, you will be uplifted by sunshine. Hardwood floors and high-end finishes are reflected in this home while a bit of Key West charm is revealed. A first-floor queen bedroom is on your left and just two steps down into the home is one of three full baths. Moving on into the oversized wet bar area and living room, you can cozy up on the sofa or chairs and watch a little TV while sipping on your wine. This beautiful space includes blue/grey cabinets, a sink, open shelving, storage, and a laundry room. Looking out through the double sets of French doors, you will enjoy the lush vegetation that surrounds this home. Moving back towards the chef’s kitchen with slide in gas range and custom hood, you have all you need to prepare a gourmet meal or simply heat up a take-out meal. A Sub-zero refrigerator and stainless-steel appliances are complemented by white upper cabinets and beautiful natural wood lowers. Quartz counters, a double oven and built in microwave enhance this room. As if that isn’t enough space, moving further towards the rear of the home and pool, is a dining room with seating for six as well as a half bath; this area is open to a cozy family room with built in cabinets, TV, and a fireplace-imagine that! A wall of glass spills out onto the beautiful blue pool area. Enjoy a day or night swim, with plenty of privacy and loungers. Cook up your catch of the day on the outdoor grill. brbrThe second-floor houses two additional bedrooms with access to the porches. The primary king bedroom has a walk-in closet, nightstands, bedside lighting, dresser storage and a TV. Its bath has dual sinks, a glass walk-in shower, and a large soaking tub, perfect for relaxing after a night on Duval Street. The queen guest bedroom has dresser storage, nightstands, bedside lighting, and a TV. The beautiful ensuite bath is tiled and includes a glass walk-in shower. brbrBED CONFIGURATION: The first-floor bedroom has a queen bed. The second floor includes a king bed in the primary bedroom and a queen bed in the second bedroom. brbrOUTDOOR AMENITIES: Lush landscaping provides privacy around the pool with lounge chairs and gas grill. The pool is heated seasonally (November-April) for an additional fee which will be assessed at the time of booking. An outdoor shower completes the Key West vibe!brbrPARKING: There is no designated parking space, but street parking is available throughout the neighborhood.brbrLOCATION: Old Town, north of Truman Ave in a quiet residential area within walking or biking distance of several shops, galleries, and restaurants. 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.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***
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Bath 3

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Sleep 6

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$993.3

/ Nightly
Private Vacation Home

JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!

Key West, Florida, United States

BEDAZZLING COMPOUND...brTwo delightful conch style island homes are situated on one glorious parcel in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Each home features 3 bedrooms with private bathrooms, as well as their own heated pools. Quintessential charm abounds and captures your island soul, with stunning pathways through lush gardens.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brFront House (PEARL): Enter the Pearl Cottage from its embracing wraparound porch, with ample seating and an invitation to relax and unwind in paradise. Sophisticated island style punctuates this 1279 sq. ft. home, complete with a modern and fully-stocked kitchen that overlooks a cozy living area with couch, love seat, cushioned chair and a smart TV for your viewing pleasure. There is a half bath with a stacked washer and dryer just off the living area for your convenience. These homes are equipped with Roku TV.brbrBack House (AMBER): Enter the newly built two-story Amber Cottage which boasts 1714 sq.ft. of living space. Enjoy a large, state-of-the-art kitchen that houses every appliance and tool needed for your culinary expression. This flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs space. An upstairs balcony resides on the upstairs landing and overlooks the pool.brbrThese homes have mounted outdoor cameras but are NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS…brFront House (PEARL): There are 3 bedrooms, two with queen beds and one with a king bed, all with private bathrooms with showers, ample storage space and TVs. A sleeper sofa resides in the living room with a powder room nearby.brbrBack House (AMBER): There are 3 bedrooms total. There is a downstairs queen bedroom (Murphy bed) with an office space and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other a king) and ensuite bathrooms with showers and large closets. All upstairs bedrooms enjoy a TV for your late night down time. A sleeper sofa resides in the living room.brbrOUTDOOR LIVING…brLose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. Each home has its own private pool that can be heated in the winter months and plenty of outdoor seating for gazing at the stars and al fresco dining. The rear home (AMBER) comes with a spa and outdoor shower as a great way to end your day in Paradise.brbrPETS...brThese homes are dog friendly only and a pet fee is required. Please include the size and breed in the comments when inquiring and booking. 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...brThere is a driveway that will accommodate 2 vehicles.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. 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).brbrBRING ALL YOUR LOVED ONES…
Bed 6

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Bath 6

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Sleep 16

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Exceptional(5)

$533.04

/ Nightly
Private Vacation Home

AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w/ Pool!

Key West, Florida, United States

AN ISLAND STUNNER...brThis is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just steps away from all the Duval Street happenings and the historic Seaport. This two-story gem offers 1714 sq. ft. of authentic island charm, with magnificent hickory hardwood floors throughout and whitewashed interior cypress wood interior walls. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter the home to a gorgeous and spacious contemporary kitchen which is a dream come true for culinary aficionados. This space is well-stocked with every modern appliance and cooking tool you'll need to concoct special meals for loved ones. This space flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs. A lovely balcony resides on the upstairs landing and overlooks the pool area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS: brThere is a downstairs bedroom with an office space, queen Murphy bed and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other with a king bed), ensuite shower bathrooms and large closets. The larger primary bedroom upstairs houses the washer and dryer in its oversized bathroom and also has a private door to the upstairs balcony. All upstairs bedrooms enjoy TVs. A sofa sleeper lies in the living room.brbrOUTDOOR LIVING…brEnjoy your sparkling heated pool with a waterfall feature, outdoor shower, and lounging chairs. Al fresco dining for 6 will delight your senses as you dine under sultry stars. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs are considered and a pet fee is required. Please leave the size and breed in the comments when inquiring.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...brThere is a driveway for this home for 2 vehicles.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).brbrBRING ALL YOUR LOVED ONES…
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(4)

$481.81

/ Nightly
Private Vacation Home

PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!

Key West, Florida, United States

CONCH STYLE CHARM...brThis is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Abundant tropical foliage embraces the wrap-around front porch, inviting you to sit and people watch with your favorite beverage in hand. Wood floors and painted white walls line the space of this 1279 sq. ft. home that features vaulted ceilings and wooden beams and loads of Key West sunshine spills through multiple skylights.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brSophisticated island style greets you as you enter the home which features a beautiful, modern kitchen, complete with island, stainless appliances and everything you'll need to cook for friends and family. The adjacent living/ area offers plush seating with a couch (also a sleeper sofa), loveseat and cushioned chair and smart TV for your viewing pleasure. A stacked washer and dryer occupy the half bath which is located just off the living area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS…brThere are 3 bedrooms, two with queen beds and one with a king bed. All bedrooms come with private en suite bathrooms with showers, ample storage space and two of the rooms include a TV. brbrOUTDOOR LIVING…brEnjoy your covered porch with a beautiful heated pool and outdoor dining for 6 as well as loungers for lazy afternoons. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs are permitted and a pet fee is required. Please leave the size and breed in the comments when inquiring or booking. 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 come with parking therefore guests must locate parking on the street in the surrounding neighborhood.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).brbrPICTURESQUE RETREAT…
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(7)

$298.74

/ Nightly
Private Vacation Home

LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a 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: Located less than two blocks from Duval Street, this fully renovated home in Historic Old Town is walkable to many of the island’s attractions, including restaurants, bars, and shops. A 2016 recipient of The Historic Florida Keys Foundation’s Preservation Award, this home has been updated with the modern amenities of a luxury vacation home while maintaining much of its architectural detail. brbrThe inviting front porch is a wonderful place to enjoy morning coffee or people watching. After a day on Duval Street, you will enjoy kicking back and unwinding in the living room with a flat screen TV. A white kitchen with plenty of counter space, cabinets and a farmhouse sink make snack or meal preparation a breeze. Groceries and sundries may be purchased at the unique Fausto’s Market, just a three-block walk or bike ride away. brbrEach bedroom has two closets, night tables and bedside lighting. The primary bedroom has a private entrance and a vaulted ceiling that adds volume to the space. The primary ensuite bathroom has natural light and includes a double vanity and a frameless, walk-in shower. The secondary bedroom includes a charming window seat, perfect for evening reading. Its bathroom has a tub/shower combination, pedestal sink, and a large, frosted window. brbrLight and bright both inside and out, this home is fenced, landscaped, and adorned with a private heated pool with waterfall feature. A covered lanai and decking will inspire you to entertain or dine al fresco. A large retractable awning provides an additional dining space or a respite from the Florida sun. Hardwood floors, central air conditioning, a mini-split in the primary bedroom, and ceiling fans add to the cool convenience of this Key West style home in paradise. brbrBED CONFIGURATION: There is a primary king bedroom, a secondary queen bedroom and a queen sleeper sofa for an occasional guest or children. brbrOUTDOOR AMENITIES: The home is fenced, and the outdoor area is private. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A covered lanai, loungers, outdoor seating, dining tables, electric grill and a Zen like garden complete the area. brbrPARKING: There is no designated parking however on street parking may be available in the neighborhood. brbrLOCATION: Old Town Key West, just 2 blocks from Duval Street. 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.br***Please note that the cleaning fee includes a full mid-stay clean***br***Managed by Historic Key West Vacation Rentals***
Bed 2

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Bath 2

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Sleep 6

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$225.7

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Private Vacation Home

The Tipsy Mermaid at Key West Golf Club

Key West, Florida, United States

Welcome to Tipsy Mermaid, your tropical retreat in the heart of the Key West Golf Club community. This stylish two-story townhome sits right on the fairway, just minutes from the island’s famous beaches, dining, and nightlife.brbrStart your day with coffee on the front porch rocking chairs, enjoy a shaded afternoon on the wraparound screened-in veranda, or savor sunset dinners on the garden patio surrounded by lush palms and lake views. With three private outdoor spaces, there’s a perfect spot for every mood.brbrInside, the home is freshly updated with coastal-chic décor, elegant furnishings, and modern touches throughout — from quartz countertops and stainless-steel appliances to luxurious glass-enclosed rain showers. The open-concept living area is perfect for gathering, cooking, or simply unwinding after a day in the sun.brbrStep across the street to take a dip in one of two resort-style community pools or squeeze in a workout at the clubhouse gym. Stroll the scenic walking paths, tee off at the golf course, or hop on a bike for a quick ride into Old Town.brbrDog friendly (1 allowed - no other types of pets allowed)brbrPlease let us know if there are any specific dates you would like or to tailor your stay- simply send us a message through the channel ! Open to off season longer terms stays or booking next season in advance as well! Come enjoy the laid back sunshine and all Key West has to offer! If you would like suggestions of things to do while you are here or to book any excursions we are happy to help!
Bed 3

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Bath 2

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Sleep 6

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$422.13

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Private Vacation Home

**WATERFRONT WHISPERS @ GULFVIEW** Waterfront Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrWATERFRONT WHISPERS captures the essence of island living within a private gated community situated on the water where you can’t hear a whisper. This 4 bedroom premium waterfront home blends total tranquility with easy access to the waters of the Florida Keys via a private boat dock. Spend your days relaxing in the pool or out on the boat, and your evenings taking in the Key West sunset from the dock. The sleek interior provides an open and airy layout, perfect for entertaining a large group. Combined with Last Key Realty's Five-Star Guest Services & In-house Concierge, your month at WATERFRONT WHISPERS will be filled with cherished memories.brbrTHE LIVING AREA & KITCHEN…brbrSteeped in natural light, the spacious, open-concept first floor immediately captures your attention with breathtaking water views framed by oversized sliding glass doors. The inviting living area serves as the perfect central hub, offering comfortable seating arranged around a large flat-screen TV. Steps away, the chef's kitchen is fully-equipped with stainless steel appliances and every culinary tool required to whip up gourmet meals. Guests can gather at the large dining table that comfortably seats eight or grab one of the three barstools at the kitchen bar for a quick bite.brbrDesigned with versatility in mind, the first floor also hosts a private den/home office. This dedicated workspace ensures a quiet retreat for those needing to catch up on remote work, while the plush Queen-sized sleeper sofa will comfortably accommodate extra guests. A convenient half bathroom is located just off the living area.brbrTHE BACKYARD, POOL & DOCK…brbrAs impressive as the interior is, the real showstopper of WATERFRONT WHISPERS is the outdoor space. Featuring an in-ground heated pool that overlooks the Gulf, it’s easy to see why this will be a primary gathering space for your group. The pool can be heated or chilled to your preferred temperature ensuring a comfortable swim year-round. For the sun worshipers, there are plenty of chaise lounges for laying out on the spacious pool deck. When you’ve had enough sun, retreat to the covered back porch with comfortable seating options. brbrThe most unique feature of this home is the private boat dock that stretches out from the back of the property. The dock is perfect for keeping your boat or boat rental right in your back yard during your vacation. The size of the boat being docked here is restricted to a shallow draft, 21-foot maximum length. The boat dock includes a fish cleaning station, power, and water. The outdoor shower is perfect for rinsing off after the pool or a day on the boat.brbrTHE LOCATION…brbrAll of this splendor in a centralized mid-island location, within the quiet residential gated community of Gulfview. You’ll be away from the hustle & bustle of Duval St, yet only be a short 10 minute drive or Uber ride down to the heart of the action. There’s one dedicated covered parking space included.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: King bed, flat screen TV, closet, private balcony with water view and en-suite bathroom.brbr** Second Bedroom: Queen bed, flat screen TV, closet, private balcony, and access to the hall bathroom.brbr** Third Bedroom: Queen bed, flat screen TV, closet and access to the hall bathroom.brbr** Fourth Bedroom: Queen bed, flat screen TV, closet and access to the hall bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** Flex Room/Home Officebr** Boat Dock (max length of 21 ft)br** Fish Cleaning Stationbr** Propane BBQ Grillbr** Private Heated/Chilled Poolbr** Outdoor Showerbr** Covered Parking Space for 1 VehiclebrbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 10 adultsbr** 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 4

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Bath 2

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Sleep 10

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Exceptional(1)

$283.18

/ Nightly
Private Vacation Home

Blue Duval walking distance to Duval St

Key West, Florida, United States

Welcome to Blue Duval a downtown Key West Home just Steps to Duval Street & Hemingway House!brbrPROFESSIONAL Monthly rental ONLY: We specialize in 30-day stays. To ensure calendar continuity, we require all residencies to align with the 1st of the month. Stays not starting on the 1st must be approved by management prior to bookingbrbrBackyard is off limits and glass sliding door to remain closedbrbrThis brand-new 1,460 sq ft modern conch cottage fuses timeless Key West architecture with sleek luxury amenities.brbrNestled in the heart of Old Town, 176 yards (under 3-minute stroll) to Duval Street`s iconic bars, restaurants, galleries and more—plus, the legendary Ernest Hemingway Home & Museum is just .2 miles away (a quick 5-minute walk).brbrBEDROOM CONFIGURATIONbrBedroom 1 - King bed with ensuite bathroombrBedroom 2 - 2 Twin XL with ensuite bathroombrbrAdditional bedding: Pull of Queen size Sofa bed (60x72)brbrHIGHLIGHTSbr- Newly Constructed in quiet neighborhoodbr- Key West Style Housebr- Dedicated 1 parking space (rarity in Key West)br- Walking distance to downtown Duval St, bars and restaurants.br-Fully equipped kitchen: drip coffee, electric kettle, all pots/pans/silverware/dishwarebrbrAMENITIESbr- 5-star amenities and furnishingsbr- Modern finishes and luxury appliances throughoutbr- 2 bedrooms & 2.5 bathroomsbr- Fully stocked kitchenbr- Wall-to-wall floor-to-ceiling retractable glass doors in the living room (Currently off limits and not for use)br- Dining Roombr- Designated dedicated parking spot (Not suitable for large SUV or truck)(Right side facing houses)br- Fast Wi-Fi internet 400-600 mbsbr-75 inch Smart TVbr- In-unit washer & dryerbr- Room-darkening shades in all roomsbr- Central A/C + ceiling fans throughoutbr-Starter Set for monthly staybrbrMove-in ready—everything is brand new and pristinebrNo car required. This unbeatable spot on quiet Amelia St puts Hemingway`s world and Duval`s energy right at your doorstep.brbrMonthly rental | Fully furnished | No pets | Non-smokingbrContact for rates and specials and secure your 2025-built Key West escape!brbrMin 29 nightsbrbrOur villa is only for responsible guest who will respect and not damage the villa and property. Guest booking must be 21 years or older. No Pets. No parties or events. No Smoking or Drug use on property. No fireworks allowed.brbrEVENTS & COMMERCIAL PHOTOSHOOTS: Are not permitted brbrA refundable security deposit is collected upon booking can be used to cover any damage that occurs during the stay. Automatically refund after 7 days after stay if no damages occur. Rental agreement must be signed and security deposit provided prior to check in.
Bed 2

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Bath 2

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Sleep 6

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$1370.24

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Private Vacation Home

Waterfront 4 Bed 4 Bath Home in Key Cove Landings

Key West, Florida, United States

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Sailor's Son. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.brbrUNIQUE FEATURES:br2 EnSuite bedrooms, both facing the water with porch access. br4 Full Baths.brbrThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 8 diners, with additional seating for 6 at the kitchen bar. brThe master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 8 adults.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).
Bed 4

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Bath 4

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Sleep 8

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Exceptional(51)

Select Dates for Price
Private Vacation Home

**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrResembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana – all of which are hidden amongst dense tropical foliage to provide ultimate privacy for your group. Speaking of privacy, each bedroom in this impressive home is designed as a private Suite, with an en-suite bathroom and access to a private covered porch. It’s easy to see why PLANTATION TROPICALE is the perfect vacation setting for those looking for a secluded tropical oasis. brbrTHE LIVING AREA & KITCHEN... brbrThe main living area of PLANTATION TROPICALE has two sets of French doors that open to the gardens and fill the space with natural light. A large SMART TV hangs on the wall in front of the plush sectional sofa, which pulls out to a Queen sleeper to accommodate extra guests. The indoor dining table sits just beyond the living room and seats six comfortably. Follow the hallway from the living area to the airy galley-style kitchen. This fully equipped kitchen with multiple sets of French doors offers all of the appliances and tools needed to prepare meals from home.brbrTHE POOL AREA.... brbrThe 28 x 14 private pool is available heated, and is large enough for everyone in your group to swim around in both the sun and shade. The spacious pool deck has chaises for lounging in the sun and a four-top dining table when you want to enjoy a poolside meal. Then, there’s the covered cabana with additional chaises for relaxing in the shade. Finally, there's a propane gas grill and outdoor dining set situated within the gardens when you want to enjoy a BBQ. brbrTHE LOCATION…brbrThe Casa Marina East district of Key West is a quiet, mostly residential neighborhood on the southern side of the island. Just a quick three block walk from the start of Higgs Beach at White Street, and just down the street from Smathers Beach, PLANTATION TROPICALE is a dream for beach-lovers who prefer to pack their coolers and towels and walk down to the sand and water. Watch the sunset from Smathers Beach or the White Street pier just around the corner. Take the short stroll to Salute Ristorante for a beach-side meal, or ride bikes down to Duval Street or the Historic Seaport for the most popular Key West attractions.brbrTHE ACCOMMODATIONS... brbrThis sprawling estate features four bedrooms in the main house and a detached guest house. Each bedroom in PLANTATION TROPICALE has an en-suite bathroom, flat screen TV, closet, and a private covered porch. Spread out in the following accommodations:brbrFirst Floorbrbr** Bedroom #1: Two Twins OR One King. En-suite bathroom has double sinks and a shower and tub combo.brbr** Bedroom #2: Queen bed En-suite bathroom has a walk-in shower.brbr** Guest House: Queen bed. En-suite bathroom has a walk-in shower.brbrSecond Floorbrbr** Master Bedroom: King bed. En-suite bathroom has double sinks and an oversized shower.brbr** Bedroom #5: Queen bed. En-suite bathroom has a walk-in shower.brbrbrALL 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** Fully Fenced and Lushly Landscaped Private Yard br** Private Pool with available Pool Heatbr** Off-Street Parkingbr** Propane BBQ GrillbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 12 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 6

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Bath 5

Bath

Sleep 12

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Exceptional(33)

$383.4

/ Nightly
Private Vacation Home

A LATITUDE ADJUSTMENT @ THE TRUMAN ANNEX

Key West, Florida, United States

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six is located in the beautiful community of Truman Annex. This gated community offers the security and tranquility that you would expect on a vacation, yet you are just steps from exploring all that Key West has to offer. Location, location, will be neighbors with the Harry Truman Little White House where President Truman spent many summer days vacationing during his Presidency. The famous Duval Street scene and surrounding blocks encompassing hundreds of restaurants/pubs/shops are only minutes away by foot. Mallory Square, with its nightly entertainment and picturesque sunsets which make Key West a popular destination are just three blocks away. Swimming, snorkeling, parasailing, fishing, and the heated pool are nearby for your enjoyment. Fort Zachary Taylor State Park and one of the best beaches in Key West are just 1/4 mile away. Bicycle and golf cart rentals are aplenty as there is no need for a car. If driving down the scenic Florida keys and keeping the vehicle for your stay, you have the luxury of a reserved, private parking space during your stay. The first floor features a comfortable living room with 60 inch HDTV, sleeper sofa,and half bath. The impeccably appointed kitchen has all housewares items such as pots, pans, and towels. Cable service and high speed wireless internet are available on each floor. The second floor Master Suite has king sized bed, 40 inch HDTV, ensuite bath and french doors that open to private balcony overlooking the tropical landscaping on Front Street. The hallway has a washer/dryer. The third floor suite features two twin beds which can be converted to king size bed depending on your needs. Private ensuite bath and large windows overlooking Front Street as well as a 32 inch HDTV complete this relaxing room. Whether this is your first visit to Key West, or returning for your 'Latitude Adjustment', this newly renovated home at The Foundry in Truman Annex is just what the doctor ordered! brbrPlease note: This property has a 28 night minimum stay
Bed 2

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Bath 2

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Sleep 6

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Exceptional(7)

$183.9

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Private Vacation Home

Quiet Conch House in Historic District

Key West, Florida, United States

Discover a piece of paradise with a beautiful conch home located in the historic district of Key West.brbr4-bedrooms, 2 baths and an open concept kitchen/dining area. Enjoy a nice sunny day on the patio or a rainy night on the front porch. Multiple fruit trees with outdoor security cameras (located: Front entrance, back near deck, and in the back house) for peace of mind. brbrGuests will be given their space for the duration of the stay. If guests would like to receive additional cleaning during their stay, they will need to email or text me.brbrGuests will be charged an additional $500 per cleaning, which will need to be paid prior to cleaning service being complete. House is cleaned using COVID cleaning protocols after each stay.brbrGuests who book will have access to the entire inside of the house. In addition to the front porch and back patio.brbrA long-term tenant resides in the back house, and the side efficiency is occupied by a seamstress for their business.brbrIncludes:brUtilitiesbrStackable washer and dryerbrFree Wi-FibrSmart TVbrbrbrOff-street parking for a compact vehicle or smallerbrbrGuests are within less than 1.2 miles walking distance of:br1. Duval Streetbr2. Fort Zachary Taylor Beachbr3. Mile Marker Zerobr4. Sloppy Joe’sbr5. 801 Bourbon Barbr6. Margaritaville br7. Mallory SquarebrbrAnd so much more.brbrThe rules:br1. Max capacity 7br2. Follow the city noise ordinancebr3. All dishes and towels must be cleaned and placed back in the designated areabr4. Guests need to adhere to local laws and noise ordinances. All fines incurred will be paid by the guest.brbrGuests can walk to pretty much any location in Key West. If guests need to go grocery shopping at either Winn Dixie or Publix, they should order a Lyft, Uber, or Taxi.brbrbr
Bed 4

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Bath 2

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Sleep 7

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Exceptional(33)

$2144.26

/ Nightly
Private Vacation Home

**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrAccording to the classic song, the best remedy for a belly ache is to put de lime in de coconut and drink 'em bot' up. Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME AND THE COCONUT and let us handle de rest! THE LIME AND THE COCONUT is a compound of two side-by-side private homes with a total of six bedrooms, six bathrooms, and an unbeatable location. The benefits of reserving these two homes are plenty:brbr** Two brand new fully-equipped kitchensbrbr** Two spacious living areasbrbr** Two private poolsbrbrLet the combination of Last Key Realty's Five-Star Guest Services and THE LIME AND THE COCONUT be just what the doctor ordered for your group's Key West vacation.brbrTHE LOCATION...brbrImagine being just steps from all of the shops, restaurants, and sites of Key West. Walk just one block to reach the world-famous Duval St, or take a short stroll down Simonton St to watch sunsets from the Historic Seaport. Not only will you be within walking distance of restaurants and entertainment, but you'll also be within a mile of Fort Zachary Taylor State Park, home to Key West's best beach.brbrTHE LIVING AND KITCHEN AREAS...brbrIt's apparent that these homes are special before you even enter them thanks to the gingerbread trim and whimsical front porch swings that grace the façade of each home. Inside, you'll be pleasantly welcomed to newly restored versions of Key West conch homes with bright colors, tall ceilings, and modern furnishings. Each living area boasts a large flat screen SMART TV, which can be enjoyed from the comfort of plush living room furniture. Both living room sofas pull out to an additional Queen bed for extra guests. The kitchens are fully equipped with stainless-steel appliances, along with all of the tools needed to prepare a meal at home. Each home has an indoor dining area, with seating for 6.brbrYOUR PRIVATE POOLS...brbrYour two private pool areas are fully fenced, with a large opening between the two fences that allows you to pass from house to house. Both pools are 6 X 9, perfect for dipping or congregating around for happy hour. Each pool can be heated to your liking and features a soothing waterfall. Comfortable patio furniture provide outdoor lounging options for the whole group. The two outdoor dining sets will comfortably seat 6 when you want to enjoy a meal outside.brbrTHE ACCOMMODATIONS...brbrEvery bedroom of THE LIME AND THE COCONUT is a suite with a private en suite bathroom.brbrHouse 1 - THE LIMEbrbr** First floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Third Bedroom: Two Twins OR one King bed and en suite bathroom.brbrHouse 2 - THE COCONUTbrbr** First Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Third Bedroom: Two Twins OR one King bed and en suite bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryer br** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen SMART TVs in All Bedrooms and Living areasbr** Fully Equipped Kitchens with Gourmet Appliancesbr** 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 includes, but is not limited to, the amenities on this list:brbr** 2 Private Pools with available Pool Heatbr** 2 Kuerig Coffee Makersbr** 2 Queen Sleeper SofasbrbrOther Notes:br** In person welcome when possible, after hours check in availablebr** Interim housekeeping and grocery delivery/provisioning provided upon requestbr** This property will accommodate up to 16 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** These homes do not include designated parking for vehiclesbr** 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 8

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Bath 7

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Sleep 16

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$298.71

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Private Vacation Home

Cool Change

Key West, Florida, United States

Summary:brbrTropical 3BDR/3BA Home with Large PoolbrbrbrbrThe Space:brbrTucked within lush tropical gardens, this stunning two-story vacation home is designed like a luxury resort or yoga retreat — a place where nature, comfort, and tranquility come together in perfect harmony.brbrbrbrStep through the doors into a light-filled open-concept living space where the living room, dining area, and kitchen flow effortlessly together, creating the ideal setting for easy entertaining or peaceful relaxation. The modern interior is styled with zen-inspired décor and natural materials, giving the home a calming, spa-like feel from the moment you arrive.brbrbrbrOn the first floor, you’ll find two beautifully appointed guest bedrooms, each with its own private bathroom, offering both comfort and privacy. Upstairs, the entire second level is dedicated to the master suite — a luxurious retreat featuring a spacious king-bedroom, a spa-inspired bathroom with both shower and soaking tub, a walk-in closet, and a private porch with plush lounge seating overlooking the gardens and the pool.brbrbrbrOutdoors, the property is nothing short of magical. The pool, designed to resemble a natural pond, is surrounded by peaceful terraces and tropical greenery, creating a soothing oasis for relaxation. The lower terrace offers sun loungers perfect for lazy afternoons, while the upper terrace features a dining area ideal for open-air meals. Fire up the high-end stainless steel grill for a casual cookout, or simply unwind surrounded by the sounds and scents of nature.brbrbrbrEvery window in the home frames a view of the surrounding gardens, turning the lush landscape into a living backdrop and enhancing the home’s serene atmosphere. Whether you’re practicing morning yoga by the pool, sharing meals under the stars, or simply soaking in the peaceful ambiance, you’ll feel as though you’ve escaped to a private luxury spa retreat — but with all the comforts of home.brbrbrbrAdditional amenities include a garage for guest use and plenty of thoughtful touches throughout the home to make your stay effortless and restorative.
Bed 3

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Bath 3

Bath

Sleep 6

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