Vacation Rentals By Owner In Key West, FL

Luxurious Renovated Monthly Rental at 1800 Atlantic – Ocean Views & Premium ComfortbrStep into elegance at this beautifully renovated, high-end condo at 1800 Atlantic. From the moment you enter, you'll appreciate the meticulous attention to detail and modern upgrades throughout the space.brEnjoy serene views of the Atlantic Ocean and lush complex grounds from your private balcony—perfect for morning coffee or evening relaxation.brbrProperty Features:br Master Suite: br King-size bed, flat-screen TV, and a beautifully renovated en-suite bathroom with a spacious walk-in shower and double vanity.brbr Guest Bedroom: br Two twin beds and a flat-screen TV—ideal for family or guests.br br Gourmet Kitchen: br Fully equipped with stainless steel appliances, including a brand-new dishwasher, and everything you need to cook and entertain in style.brbr Living Area: br Bright, open space with comfortable seating, flat-screen TV, and easy balcony access.br br Technology & Comfort: br High-speed wireless internet and flat-screen TVs in every room.br br Laundry: br Full-size washer and dryer in unit for your convenience.brbr Air Conditioning: br Serviced yearly with a deep coil cleaning and upgraded with a UV light system to ensure air quality and prevent mold.brbr Water Filtration: br A newly installed whole-house water filter provides clean, filtered water throughout the unit.brbrbrThis condo is the perfect blend of comfort, style, and peace of mind. Ideal for a monthly getaway or an extended stay in paradise. brPlease Note: This property has a 30 day minimum stay requirement.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.

Margaritas in Paradise Monthly Retreats with Ocean Views at 1800 Atlantic

Key West, Florida, United States

Bed

Bath

Sleeps

$300.2

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. To explore the first-floor home, search for “Poinciana Garden” or book “Poinciana Paradise” to reserve the entire home for family or friends. brbrWalkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered porch with a treetop view. Prepare meals in the bright and sunny kitchen with built in corner hutch, open shelving, and gas range. With so many local dining options, you won’t even mind being without a dishwasher. An open concept living area with vaulted ceilings provides natural light and adds to the airy ambiance of your vacation home. This area is cooled by a brand new mini-split AC and ceiling fan. The primary bedroom includes an ensuite bath, TV, nightstands, brand new mini-split AC, and ceiling fan. Stroll through its French doors onto the private porch and enjoy the Florida breeze with a delightful book. Sun yourself in the shared yard or take a jaunt to the beach. When the day is over, you may find yourself relaxing under the stars and enjoying conversation with newfound friends. brbrBED CONFIGURATION: The king bedroom has an ensuite bathroom with a tub/shower combination and a mini-split AC. There is a sleeper sofa in the living room for a child or guest. brbrOUTDOOR AMENITIES: Open the French doors from your bedroom and step out onto the second-floor covered porch. The backyard features a shared gas grill, washer and dryer, lush garden, chaise lounge chairs, and outdoor dining set.brbrPARKING: There is on-site parking for one small car as well as a bicycle rack for your convenience. Please note this home is on a tiny, one-way lane. brbrLOCATION: Historic Old Town, North of Truman and 2 blocks from the excitement of Duval Street. A majority of the best Key West attractions are located here as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch style homes. You will enjoy being right in the middle of everything!brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

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

Key West, Florida, United States

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Select Dates for Price

This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through breeze and expansive views of the tropical courtyard.brAs assigned private parking space will convey with your rental. You can feel secure in our fortress or a property.brKey West is an Island with so much to offer, perfect for the Sports enthusiast with fishing, diving, snorkeling and so much more. run along our coast or take a leisurely bike ride and meander through our historic streets. brbrEnjoy a cocktail and listen to our talented live musicians.brbrStroll through our museums and galleries. brbrKey west is here to help you enjoy every minute, it is hard to leave and will never go away.brWhen you re-visit we ill be waiting.brbrNicely renovated with many of the comforts of home. Wireless Internet.brThis property has a 28 day minimum stay requirement.

Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF

Key West, Florida, United States

Bed

Bath

Sleeps

$174.34

Spacious 2-Bedroom Condo with Ocean Views & Island ComfortsbrbrThis beautiful 2-bedroom, 2-bath condo offers a lovely view of the Atlantic Ocean and an extra-large floor plan with a slightly oversized private balcony—accessible from both bedrooms and the living room. It’s the perfect island retreat with all the comforts of home.brbrEnjoy a full-size, fully equipped eat-in kitchen and a full-size washer and dryer for added convenience. Whether you're here for a short stay or an extended escape, this condo provides the space and comfort you need to truly relax.brbrKey West offers something for everyone:brFrom its rich literary and artistic history to live theatre, museums, and exciting water sports. For thrill-seekers, even skydiving adventures await. Enjoy world-class restaurants, a laid-back atmosphere, vibrant live music, and a welcoming, safe environment—all with perfect winter temperatures in the only frost-free city in the continental U.S.brbrCome visit paradise. We promise you won’t regret it.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.

Charming 2 Bdrm Oceanfront Oasis Key West Beach access Old Town Bike ride.

Key West, Florida, United States

Bed

Bath

Sleeps

$891.72

THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all! Close to the sights and sounds of Duval Street yet quietly surrounded by Bougainvillea and palm trees, you will love this location. The fenced property with private pool has 4 bedrooms and 2.5 baths. It’s perfect for vacationing with friends or kiddos who will enjoy the second-floor bedrooms with a Jack and Jill bath. The open concept living room/dining room has plenty of seating and a view of the pool area. The sunny kitchen has modern conveniences, stainless steel appliances, white cabinets, and outdoor access. brbrThe primary first floor king bedroom is adorned with two nightstands and bedside lighting. An armoire for storage, outdoor access and a private ensuite bath add to its convenience. A tiled walk-in shower, pedestal sink and dresser storage complete the bath. In the event you need to keep an eye on a little one or an elder, the first floor has a cozy twin bedroom off the kitchen with a small dresser and bedside lamp. A stackable washer/dryer is conveniently located on the first floor. The second floor is home to two additional bedrooms with sloped wood ceilings and a shared Jack and Jill bath. One queen bedroom includes two bedside tables with lamps and dresser storage. The other bedroom includes two twin beds, a small dresser with a lamp, storage, and a view of the palm trees. brbrThis delightful Key West cottage style home with Dade County pine accents will allow you to genuinely enjoy the Florida lifestyle. With French doors that open onto the pool and sunshine, come enjoy your own slice of paradise! brbrBED CONFIGURATION: The first floor includes a primary king bedroom with ensuite bath as well as a small twin bedroom and half bath. One second floor bedroom is a queen and the other is a twin. Second floor bedrooms share a full Jack and Jill bathroom with dual sinks and glass walk in shower. *Please note this home has no tub for bathing toddlers/young children.*br brOUTDOOR AMENITIES: The pool with waterfall feature is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Decking surrounds the pool for sunbathing and a grill is available for outdoor meals. A furnished, covered cabana with ceiling fan provide a respite from the sun or a wonderful place to nap.br brPARKING: There is designated off-street parking for one mid-size car.br brLOCATION: Old Town, north of Truman Ave, near restaurants, shops, and galleries. Walkable to Duval Street, the Ernest Hemingway House, and the Key West Lighthouse. This home is near to the Butterfly and Nature Conservatory as well as the Southernmost Point, one of the most photographed attractions in KW.br brPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.br br***Guests must be 25 years of age or older unless accompanied by an adult.br***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not active inside the property nor at the pool area.***br***Managed by Historic Key West Vacation Rentals***

Cottage

~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

Key West, Florida, United States

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Bath

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Select Dates for Price

Keys to Paradise: A 5-Star Beachside Retreat in Key West brbrWelcome to Keys to Paradise, a luxurious 3-bedroom, 2-bath condo nestled in a private oceanfront resort—just steps from the beach and minutes from the charm of Old Town Key West.brbrThis direct oceanfront condo offers a master suite featuring a king-size bed, jacuzzi tub, and a spa-style walk-in shower. Two additional bedrooms each include queen-size beds, breathtaking ocean views, and sliding doors leading to the expansive balcony. The second bathroom also features a large, modern walk-in shower.brbrStep onto the spacious private balcony and take in panoramic views of the aquamarine sea, breathtaking sunsets, and soothing coastal breezes—a perfect setting for your morning coffee or evening cocktails.brbrThe fully equipped gourmet kitchen includes:brbr Stainless steel appliancesbr Double ovenbr Bosch dishwasherbr Granite countertopsbrbrIt opens into a bright and airy living room with floor-to-ceiling sliders that showcase views of the ocean and mangrove sanctuary.brbrAdditional features:brbr Cable TV, high-speed internet & WiFibr Washer & dryerbr Starter supplies & fresh linensbr Assigned garage parkingbrbrResort-Style Amenities:brbr Heated oceanfront poolbr Hot tub & restroomsbr Private beach accessbr Tennis & handball courtsbr Charcoal grilling stationsbr Recreation roombr On-site securitybrbrLocation Highlights:brbr Steps from Smathers Beach (with rentals for paddleboards, catamarans, parasailing & more)brbr Adjacent to scenic jogging & walking pathsbr 1 mile to White Street fishing pierbr 2 miles to Mallory Squarebr Close to supermarkets, shops, restaurants, and water-sport chartersbrbrWhether you're looking to relax or explore, Keys to Paradise offers the perfect blend of luxury, location, and comfort. Your unforgettable Key West escape starts here!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.

Key West Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo

Key West, Florida, United States

Bed

Bath

Sleeps

$244.98

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$289.9

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

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

Key West, Florida, United States

4

Bed

3

Bath

4

Sleeps

$270.08

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$286.29

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.brbrNeed to stay connected during your trip We offer high speed cable internet.brbrLocated within the gated community of Truman Annex, you are just steps away from the new Truman Waterfront Park and only 2 blocks from the famous Duval St. Enjoy the heart of Old Town Key West and all its charms! Stroll or bike to many of the historic sites such as Hemingway House and Little Truman White House or take a relaxing sunset cruise. If you are bringing a vehicle you will have a secure parking space while you enjoy the many nearby activities.brbrAmenitiesbrbrOur Condo includes the following:brbr- Ship's Loft (Children & Teens love the privacy!)brbr- Televisions in bedroom, living area and loftbrbr- Fully equipped kitchen with granite counter-tops & stainless steel appliancesbrbr- 2 Bicycles for Guests to use during their staybrbr- Bed Linens, Bath & Beach Towelsbrbr- Hairdryerbrbr- Beach Chairs & Coolerbrbr- Full size stacked washer & dryerbrbr- Access to Shipyard Poolbrbr- Gated parking placebrbr- Secure high speed wireless internet in condo

Unique Home with loft @ Truman Annex

Key West, Florida, United States

1

Bed

1

Bath

4

Sleeps

$1564.57

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$467.06

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information. brbrThe Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. brbr2 Bedroom 2 bath suite, some renovations with flat screen plasma TV's in both bedrooms and the living room. , King bed in the Master bedroom, king in the guest bedroom and a queen sleeper sofa in the living room. Full size fully equipped eat in kitchen, washer & dryer.brbrBoth bedrooms and the living room access the spacious private balcony. Enjoy the amazing view from this top floor unit. You wont find a better value in Key West for what you get here.brbr1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersport's activities available.brbrThe property itself features assigned secure parking spaces, 3 lighted tennis courts, one of which is the only clay court in Town. There are beautiful botanical gardens with picnic and BBQ areas.brbrThe Olympic size heated pool sits on the edge of the Atlantic Ocean, There is also a 20 person bubbling Jacuzzi tub. brbrHigh speed internet access.brbrbrSMATHERS BEACH SWIMMING BEACH IS OPEN WHICH IS A 5 MINUTE WALK FROM OUR PROPERTY ****

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West, Florida, United States

Bed

Bath

Sleeps

$309.84

**Beginning 12/22/25, Fair Winds will be a MONTHLY RENTAL (28 nights within the same month). Stay a month and live like a local!brbrTHE PROPERTY: As you open the white picket gate to this three-story townhouse, your tropical courtyard and outdoor dining area will delight you. Through the oversized French doors with transoms, you will find your living room, dining area, updated kitchen and half bath. This home has more windows than most as well as vaulted ceilings, adding sunshine and volume to the open concept living area. A comfortably furnished family room with TV lead to the dining table with seating for 4-6. The galley-style kitchen has everything you need to prepare a meal or snack. brbrThe second-floor primary bedroom is beautifully furnished and includes bedside lamps, nightstands, TV, closet and dresser storage. The ensuite bath is tiled and has a shower/tub combination. Open the French doors enjoy morning coffee on your private balcony.brThe guest bedroom is sunny and bright on the third floor. Twin beds can be combined to form a king upon request. A TV, bedside table, lamp, closet, and dresser storage are also provided. br brHistory aficionados will appreciate The Truman Annex. Formerly an Army installation and later a Naval station, it was also President Harry S. Truman’s winter home. The park-like setting with an abundance of palm trees and white picket fences is a source of pride and splendor in Key West. brbrWhether you spend a day at the pool or a night on Duval Street, you won’t be disappointed with this townhouse or its unbeatable location. Come stay a while at Fair Winds at the Foundry. brbrBED CONFIGURATION: The primary king ensuite is on the second floor. The third floor ensuite guest bedroom has two twin beds that can be joined to create a king bed. A sleeper sofa in the living room can accommodate 2. brbrOUTDOOR AMENITIES: Share a fabulous pool with guests of the Foundry. Enjoy cocktails on the patio or grill up the daily catch on the gas grill. brbrPARKING: There is a dedicated covered parking space for one vehicle that may not exceed 18’ long x 80” wide. This is strictly enforced so be sure your vehicle is appropriately sized. brbrLOCATION: Tucked away in the exclusive, historic Truman Annex, this home in Old Town is close to everything. Within walking distance are galleries, shops, restaurants on and off Duval Street, sunsets at Mallory Square and the Truman Waterfront Park. Bike to Fort Zachary Taylor State Park’s beach, stroll to the Key West Harbor or walk to the Tropic Cinema and catch a film. br brPETS: 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***

~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$276.5

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$1385.21

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

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

Key West, Florida, United States

3

Bed

3

Bath

7

Sleeps

$258.91

Welcome to your perfect tropical retreat in the heart of Key West, Florida! Nestled within the renowned Shipyard condominium, Tiki Beach too offers a prime location that combines the vibrant energy of Duval Street with the family-friendly appeal of Truman Waterfront Park and the pristine shores of Fort Zachary Taylor Beach.brbrStep into a beautifully appointed condo that seamlessly blends comfort and style. The living space is tastefully decorated with soothing blue walls, creating a relaxed ambiance that instantly puts you in vacation mode. The fully equipped kitchen beckons both amateur and seasoned chefs to whip up delicious meals to dine al fresco on your back deck.brbrTiki Beach Too has two bedrooms, each set to be an oasis of tranquility, featuring plush bedding and soothing decor to ensure a restful night's sleep after a day of exploring Key West. The bathroom off the common space has a tub, while a full bath with shower is ensuite of the front bedroom. Both bathrooms are elegantly designed, offering modern amenities and a spa-like atmosphere.brbrOne of the highlights of this vacation rental is its proximity to the iconic Duval Street. Just steps away, you'll find yourself immersed in the lively atmosphere, with a plethora of shops, restaurants, and bars to explore. The Green Parrot, a favorite local and tourist hangout, being the closest, less than two blocks away. Whether you're looking for a night out on the town or a leisurely stroll, Duval Street has something for everyone.brbrFor families with children, the Truman Waterfront Park is right next door, featuring a delightful splash pad that promises endless fun for the little ones. Let the kids frolic in the water while you unwind under the swaying palm trees, enjoying the tropical breeze.brbrAnd for those seeking a sun-soaked day at the beach, Fort Zachary Taylor Beach is within easy reach. With its soft sandy shores and crystal-clear waters, it's the perfect place to soak up the sun, take a refreshing dip, or explore the historic fort that gives the beach its name.brbrYour Key West adventure awaits at Tiki Beach Too, our Shipyard condominium vacation rental – a haven of comfort and convenience in a location that puts the best of Key West at your fingertips. Book your stay now and make memories that will last a lifetime!br*PLESE NOTE THE POOL WILL BE CLOSED THE MONTH OF AUGUST, 2026.

Bring your umbrella drinks @Tiki Beach Too! Shipyard 2bed/2bath

Key West, Florida, United States

Bed

Bath

Sleeps

$238.42

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this updated property including its location in Bahama Village, private pool, and pool house.brbr As you enter your vacation home, enjoy the open concept living room, kitchen, and dining area. In addition, there is a built-in work station for homework or working from home. The kitchen has plenty of storage, stainless steel appliances, granite countertops and a peninsula for entertaining. Through the kitchen you will find the relaxing primary bedroom. Here you may slumber in the queen bed, watch TV, or enjoy a delightful book in the reading chair. The main bathroom is updated and includes a shower/tub combination in pumpkin onyx tile as well as a single vanity with granite countertop. Built-in storage drawers are conveniently located just outside the main bath. Exit from the primary bedroom to the backyard pool area. brbrThe cocktail pool is perfect for cooling off after a day on Duval Street. The outdoor shower will not only rinse you off after a swim but can serve as your pool house guest’s shower. The fenced backyard area is comfortably furnished with a dining set and umbrella for dining poolside. A gas grill is provided for the chef in your family. Natural light, air conditioning, ceiling fans and hardwood floors add to the comfort of this home away from home. Come immerse yourself in the charm of Key West from this 1923 ‘shotgun’ style home!brbrBED CONFIGURATION: There is a queen bed in the main house and a queen sleeper sofa in the pool house. brbrOUTDOOR AMENITIES: There is a cocktail pool with marble-like trim just off the covered back porch. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The deck is furnished with a dining table, chairs, and umbrella as well as a gas grill and outdoor shower. Don’t forget to do a little people watching from your front porch! brbrPARKING: No designated parking spot. On-street parking available in the neighborhood.brbrLOCATION: Historic Old Town, in Bahama Village south of Truman Ave, between the Southernmost Point and the Hemingway House. The area features beautiful historic cottages and quiet tree lined streets. Walkable to several shops, restaurants, and the community pool. 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***

Cottage

~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.

Key West, Florida, United States

Bed

Bath

Sleeps

$508.89

Escape to Key Lime Paradise, a bright, modern 2-bed, 2-bath, Sleeps 6, condo in Key West. Perfect for couples or families, it features a private balcony, a fully equipped kitchen, and a dedicated workspace. Enjoy resort-style amenities including a pool, hot tub, gym, and tennis/Pickelball court. Just a short drive from the vibrant energy of Duval Street, this peaceful retreat offers the best of both worlds. Two elevators serve the building, providing quick and convenient access to the condo.

Key Lime Paradise 2BR 2 Bath Pool Hot Tub Sleeps 6

KEY WEST, Florida, United States

Bed

Bath

Sleeps

$520.83

Key West Waterfront Paradise – FREE Boat Slip Included!brbrWake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes.brEnjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.brbrThe Spacebrbr• Primary Bedroom: King bed • Marina views • Private balcony access • Ensuite bathroom • Walk-in closet • Flat-screen TVbr• Second Bedroom: Two Queen beds • Flat-screen TVbr• Living & Dining Area: Open-concept • Bright & airy • Plenty of space to relax, play games, or dine inbr• Kitchen: Fully stocked with cookware & utensilsbr• Laundry: Full-size washer & dryer for added conveniencebrbrDockage Detailsbrbr• FREE Private boat slip with fresh water, power, and covered fish cleaning stationbr• Commercial ice maker on-sitebr• Overnight stays on boats are not permittedbrbrAmenities you’ll Lovebrbr• Shared heated poolbr• BBQ grills & tiki areabr• Free on-site parkingbr• Adjacent park with tennis courtsbr• Private building elevatorbr• High-speed WiFi br• Just 9-10 minutes from Key West Airport (EYW)brbrNearby Attractionsbrbr• Duval Street & Historic Old Townbr• Smathers Beachbr• Bayview Park – right across the streetbr• Historic Districtbr• Mel Fisher Museum & Shipwreck Museum

Waterfront Condo with FREE Slip & Pool 2B/2B in Key West with AC

Key West, Florida, United States

Bed

Bath