Vacation Home Rentals By Owner In Key West, FL

Passover Cottage | Private Pool & Ideal Key West LocationbrbrPassover Cottage is your ultimate retreat in the heart of Key West! This charming 2-bedroom, 2-bathroom vacation home offers the perfect combination of privacy and proximity to the best of the island. Just a short walk from iconic attractions like Ernest Hemingway Home and Museum and Southernmost Point, Passover Cottage lets you immerse yourself in Key West's vibrant culture while enjoying a peaceful escape.brbrThe Space:brPassover Cottage features a cozy, air-conditioned interior with everything you need for a comfortable stay. The fully equipped kitchen includes a dishwasher, perfect for preparing your favorite meals. The master bedroom boasts a luxurious king-sized bed, while the second bedroom is fitted with two twin beds. With two bathrooms featuring walk-in showers, you'll have all the amenities to feel at home. Relax in the spacious living room, or step outside to the private patio and enjoy dining al fresco by the pool. For added convenience, the outdoor space also includes a gas grill and an outdoor shower, perfect for rinsing off after a day at the beach.brbrGuest Perks:brEnjoy your own private pool to cool off after a day of exploring. Stay connected with free Wi-Fi throughout the home, and take advantage of the provided washer/dryer for added convenience. For those who love cycling, you're in the perfect location to rent bikes and explore the island's picturesque streets.brbrNeighborhood Highlights:brPassover Cottage offers a prime location, just steps from Key West's top attractions, including the Ernest Hemingway Home, Beaches, and Duval Street. Being centrally located, you can easily stroll to one of the many beaches or enjoy a night out at the island's lively bars and restaurants. Whether relaxing under the sun or exploring the vibrant nightlife, everything you need is right nearby.brbrTransportation Tips:brPlease note that there is one designated parking spot on-site. Additionally, street parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Private Washer/Dryer: Available for guest use.br- Private Parking: Enjoy one dedicated, gated parking spot.br- Family-Friendly: Suitable for families or small groups.br- Pet-Friendly: We welcome dogs (40lbs maximum) with a $20/per pet per night fee.br- Guests must be 25 years or older to reserve the property.brbrPlease note that the property is located in a peaceful, noise-sensitive residential neighborhood. To maintain the serene environment and ensure a positive experience for everyone, we kindly ask guests and neighbors alike to respect the local quiet hours and be mindful of all who have come to enjoy this wonderful neighborhood!brbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrAt Colocada Vacation Rentals, we're committed to making your stay in Key West unforgettable. Have any questions or need recommendations Don't hesitate to reach out— we're here to ensure your stay is as perfect as possible!

Passover Cottage | Private Pool & Ideal Key West Location

Key West, Florida, United States

Bed

Bath

Sleeps

$279.43

Enjoy a stylish experience at this charming 2 BR, 2 BA home with heated pool, in the heart of Old Town, Key West. You will be within a block from Duval Street, Hemingway House, Moondog, Blue Heaven and the Key West Lighthouse. Watch Key West stroll by from the private front porch or enjoy the shared pool. This 2 story house has 2 spacious bedrooms and 2 bathrooms on separate floors. The well appointed kitchen has stainless appliances. There is an outdoor grill for your use, and an outdoor dining area.brbrThis is a two story stand alone house. The first floor has a bedroom, full bathroom, living room with sofa bed, washer/dryer, and kitchen. The second floor has a bedroom and full bathroom and a nice view of the pool below.brbrYou will have sole access to the entire house, including front and back porches. The pool and yard is shared with the other five units.brbrA max of 6 people is permitted. A mid stay cleaning is required ($300 for the mid stay cleaning, $300 for the end of stay cleaning).brSo sorry, no pets. brPlease be respectful of the neighbors, they are our friends.brNo smoking is permitted inside the house or on the grounds.

2 BR Charmer w/ Pool, Old Town, Key West - A Stone's Throw

Key West, Florida, United States

Bed

Bath

6

Sleeps

$516.79

***HOA requires a minimum rental period of 6 nights and a maximum of 4 guests, and no exceptions can be made. Unit is a Sunday to Sunday rental during peak seasons. Please review additional policies below.*** brbr brbrWelcome to Life Is A Breeze – Your Tropical Retreat in the Heart of Old Town Key West! brbr brbrNestled in the charming Windward Park gated community, Life Is A Breeze is a beautifully appointed 2-bedroom, 2-bath Bahamian-style townhome surrounded by lush tropical landscaping and views of the sparkling community pool. With only 13 townhomes in this quiet, private community, guests enjoy a peaceful island retreat while still being just one block from the excitement of world-famous Duval Street. brbr brbrStep outside and you're within walking distance of Key West’s best restaurants, lively bars, boutique shopping, art galleries, and historic attractions. Rent a bicycle and cruise over to Mallory Square for sunset celebrations, or explore the Historic Seaport, both just a short ride away. Even the island’s beaches are only a quick trip from your front door, making Life Is A Breeze the perfect home base for your Key West adventure. brbr brbrInside, this spacious townhome offers an open floor plan designed for relaxation and entertaining. The bright living area features comfortable seating, a flat-screen television, and soaring ceilings that open to the second floor, filling the space with natural light. Whether you're returning from a day at the beach or enjoying a quiet evening in, this inviting living space makes it easy to unwind. brbr brbrThe main level bedroom offers convenient access along with a nearby full bathroom. Upstairs, the primary suite features a plush California king bed, flat-screen television, and an en-suite bathroom, providing a comfortable and private retreat after a day of exploring. brbr brbrGuests will enjoy all the comforts of home including WiFi, flat-screen TVs, laundry, assigned parking, and access to the impressive 20 x 50 foot community pool, perfect for cooling off under the Key West sun. brbr brbrWhether you're here to relax by the pool, explore Old Town, or enjoy the vibrant island nightlife, Life Is A Breeze offers the ideal blend of comfort, location, and tropical charm. brbr brbrCome experience the laid-back lifestyle and unforgettable beauty of Key West — your island getaway awaits. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1 (2nd Floor): King Bed, En-Suite Bathroom, Smart TV brbr brbrBedroom 2 (1st Floor): King Bed, Smart TV brbr brbrLiving Room: Sofa, Chair, Smart TV brbr brbrKitchen: Nicely Equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool brbr brbr- One Designated Parking Space brbr brbr- Multiple Porches with Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Drip Coffee Maker, Toaster, Blender brbr brbr- Linens and bath/pool towels provided brbr brbr- 1 block to Duval Street brbr brbr- 0.5 miles to Southernmost Point brbr brbr- 1 mile to Fort Zachary Taylor State Park Beach brbr brbr- 2.3 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: 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 brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited 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.

Life Is A Breeze: Gated Old Town Townhome Just 1 Block from Duval Street w/ Pool & Parking

Key West, Florida, United States

Bed

Bath

4

Sleeps

$157.69

Casa Louisa is a tropical paradise steps off the corner of Duval on Louisa Street. Walk to all of your favorite places/beaches in minutes. Relax on your private front porch with coffee/cocktail and enjoy the feel of your own home. brThis Great Location is right off Duval in what is known as the Southern Most Point district of Key West (close to the buoy). This is considered to be the best of both worlds. It is right off the famous Duval Street, but on the quiet upper end towards the beach. You can enjoy all of the nightlife that Key West has to offer and then walk right back to peace and paradise within minutes.brThis location feels like your own home with a full kitchen, living room and outdoor grill. Sit on the porch and soak in the Key West Vibe as you watch the sites go by. Enjoy your morning coffee outside on the porch and say hi to all of your new Conch Republic Neighbors. You will feel like a local in no time!

Casa Louisa - XMAS IN KW! 2 Bed in Old Town - Right off Duval/Great Front Porch

Key West, Florida, United States

Bed

Bath

Sleeps

$305.98

Paradise on Porter is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. This townhome is very convenient to all there is to do in downtown Key West. Leave your car at home because you can walk, bike or scooter 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 seating area outside. The living area has comfortable seating and a flat screen TV. The French doors open up onto the spacious deck and nicely landscaped yard. Upstairs are two bedrooms each with and ensuite bathroom, standard bed, and ample closet space. The laundry is in the upstairs hallway for convenience. brbrThe Truman Annex Waterfront Park is close by with walking paths, open areas to play or relax, or bring the kids to the splash pad or park to play. Fort Zachary Taylor State Park and Beach are also close by and offer picnic areas with grills. The beach areas are great 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 fabulous neighborhood on your next visit to Key West and be right near all there is to do on our island. This is a weekly rental. brOne parking spot per unit - No Trucks or oversized vehicles - Campers or motorhomes not allowed on property. Sorry no pets allowed per HOA.

PARADISE ON PORTER in the Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$546.4

Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and only two blocks from world famous Duval Street and its restaurants, bars, art galleries, and shops. brbrThis conch cottage has all the modern amenities you would need for a relaxing stay in Key West. brbrThe contemporary kitchen with a cathedral ceiling is equipped with a full-size refrigerator, stove/oven, all cookware, utensils, dishes, and convenient countertop appliances. The kitchen has a dining table and seating for four in addition to two stools at the breakfast bar. Glass sliding doors open to a fenced, private deck that includes a gas grill, two chaise lounges, built-in benches, an outdoor dining table, and an outdoor shower. The living room contains a queen convertible sofa. All linens and towels, including beach towels, are supplied. The home is equipped with a new stacked washer and dryer located in a bathroom closet. brbrBoth bedrooms share the common area bath, with double-basin pedestal sink and beautifully tiled walk-in shower. One bedroom has a queen bed and the other has two twin beds. Both bedrooms and the living room contain flat-screen TVs. The large front porch is a few steps above the street, making it the perfect place to sit on the wicker chairs and relax with your morning coffee.brbrThe location is ideal—just blocks from Blue Heaven and Pepe’s, the best breakfast spots in town. All the nightlife venues are located within a short walking distance.brbrPLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A POOL. You may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental.

FLEMING-O (Flamingo) Cottage is the perfect getaway

Key West, Florida, United States

Bed

Bath

Sleeps

$185.07

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 queen and 1 queen)brBathrooms: 2brLocation: Old TownbrSquare Feet: 1461brParking: Off street parking in gravel drivewaybrAmenities: Wifi, TVs, in-unit laundry, small fenced backyard, shared poolbrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Pearl in Paradise-Charming 2bed 2bath Old Town home w/ shared pool, parking

Key West, Florida, United States

Bed

Bath

Sleeps

$832.97

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brThis unit is a 2 story condo (both bedrooms upstairs).brBedrooms: 2 (1 queen and 2 twins, sleeper sofa only recommended for children)brBathrooms: 2.5brLocation: Located on Duval StbrSquare Feet: 1240brParking: One assigned parking space in gated garagebrAmenities: Wifi, TVs, in-unit laundry, shared pool, balconybrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Duval Square Condo-2 bedroom 2.5 bath, w/pool, parking, on Duval St

Key West, Florida, United States

Bed

Bath

6

Sleeps

$479.22

“Richley individual” yet “classic Key West” are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with a fabulous deck, pool, and tropical gardens. Located on a tree-lined street in the fashionable Meadows neighborhood, this property offers your best life whether that’s relaxing out-of-doors or in-doors or midway between under the open-air covered space so perfect for socializing and dining no matter what the weather. The house is located a few blocks from the White Street corridor of galleries and multiple food options and just a walk or bike ride to the world-famous Duval Street. brbrBeyond the charming white picket fence and narrow, brick-lined garden walkway is the two-story house with double front porches. Up four steps brings you to the first floor porch and chairs. Perhaps sit here with a cup of coffee or to watch locals leisurely stroll by walking their dogs. brbrAs is frequent in Key West floor plans, bedrooms are up front to leave ample room for the social areas—kitchen and the pool area—in the back. True to form, the first room inside the front-foyer alcove is a queen bedroom accessible through impressive white double wooden doors. Four windows in the room guarantee plenty of ambient light with darkening shades and drapes for when appropriate. Bedside tables and a six-drawer dresser provide space for clothing and vacation accoutrements. A flatscreen TV sits on the dresser in the perfect location for viewing from the ultra-comfy bed. A Florida ceiling fan with light globe hangs above with attractive hardwood floor below.brbrAcross the hall is a nicely appointed guest half bath. And back on the same side is the kitchen which, because of the open floor plan, also flows easily into the living area then flows into the outside pool oasis. brbrThe kitchen is perfectly designed to be easy to use and a snap to clean up. All the cooking and eating utensils you would need are put away behind cherry cabinets to retrieve easily when you are ready. The counters are granite. Above whirs a ceiling fan, with two windows, stainless steel appliances, and oodles of cabinets below. For maximum comfort, an anti-fatigue standing mat covers a lot of the wooden floor here. In a town famous for its restaurants, your vacation culinary efforts might be just warming up leftovers from an exquisite meal out the night before. Or you might decide to grill some local fish and veggies on the gas BBQ. Two bar chairs on one side of the counter make the ideal place to sit for coffee and maybe a pastry from one of Key West’s fabulous bakeries.brbrThe living room, with couch, two chairs, and a small coffee table offers a delightful area for socializing or watching sports or a movie on the large flat screen TV. Of course, there’s central AC, high-speed internet, and cable TV at your fingertips. The ceiling fans here, as throughout the house, circulates air and adds a touch of beauty and island style. As a decorative and structural feature, the much-coveted Dade County Pine walls are impressive here as well as throughout the home.brbrOne wall in this room is composed of three large glass and wooden French doors opening onto the deck, pool, and tropical gardens. A roof extension from the house provides a covered area right on the other side of the glass wall. With cushioned seating and large wrought iron dining table, you may find yourself spending most of your time here talking, playing cards, maybe BBQing something luscious. Except, that is, for the times you spend swimming or floating in the temperature-controlled pool. Or the times you sit in one of the Adirondack chairs facing the pool to work on a tan or to watch puffy white clouds float over in a blue sky. Midday the landscape palms cast an occasional palm frond reflection on the sparkling surface of the pool. It’s your own private piece of paradise. Two sets of fences and a perimeter of green foliage create privacy and security. brbrThere will come a time in the evening when you are interested in sleeping. For that time of night there’s the first-floor bedroom or one of the three bedrooms up a grand staircase to the second floor. Front and center on the second floor is the door to the balcony. Like the porch on the first floor, this is a great spot to sit and enjoy nature. It feels like you are suspended in the treetops but still have a view of comings and goings on the street below. The second door opens into the second queen bedroom with a closet, chest of drawers, copious windows, and a delightfully comfortable bed. A similarly delightful bedroom follows. Both have easy access to a full bath accented with blue and white ceramic tile. And at the back of the second floor overlooking the pool is an impressive master bedroom. It features an inviting King bed, ensuite bath, laundry closet with washer and dryer, and plenty of storage for clothing and other travel accoutrements. As with every other bedroom, this one features a flat screen TV perfectly positioned for viewing from the bed.brbrDon’t rush (because no one rushes on a tropical island), but when it’s time to explore the island, you’ll find yourself conveniently located a few blocks from the White Street corridor with shops, galleries, and good eating. To your left as you face White and down seven or so blocks is the White Street Pier which juts out a quarter mile into the Atlantic. Turning to the left and down five blocks or so puts you a block away from the Gulf of Mexico. But the most fun street is the world-famous Duval which runs the whole width of the island from beach to beach. Here’s where you’ll find what Key West is famous and infamous for: tours, beaches, museums, water sports, shopping and bars. Maybe visit the Aquarium where you can pet a shark. Or let butterflies land on your shoulder at the Butterfly Conservancy. Numerous restaurants, many with open-air seating, some right on the water, offer a plethora of food and drink options. The island also offers plenty of cultural activities as well such as live music, art exhibitions, and plays. Perhaps catch a movie on one of the three screens at the Tropic Cinema. Or stop in at Books & Books to catch a glimpse of local authors. brbrThe Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information. brbr**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.

Boomerang Boathouse - Located in The Meadows

Key West, Florida, United States

Bed

Bath

Sleeps

$1114.77

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrKey West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom layout, a private pool, and plenty of space to stretch out or come together as a group. In addition to the fabulous layout and desirable amenities, this home has an unmatched location. THE ZESTY LIME combined with Last Key Realty's Five-Star In-Home Guest Services is sure to make your group's stay in Key West an extraordinary one.brbrNeed more space Rent both THE ZESTY LIME and THE TOASTED COCONUT together as THE LIME AND THE COCONUT - two side-by-side private homes that can sleep a total of 16 guests with two private pools.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 AREA AND KITCHEN...brbrFrom the street, this home's classic Key West architecture boasts the gingerbread trim and whimsical porch swings that define Old Town conch homes. Upon entering, you'll be pleasantly welcomed into a newly restored version of a Key West conch home. The living area boasts a large flat screen SMART TV, which can be viewed from the comfort of plush furniture. The brand-new kitchen features stainless-steel appliances and all the tools needed to prepare a meal at home. The indoor dining table has seating for up to six. There's also a convenient powder room located in the hall.brbrYOUR PRIVATE POOL...brbrPrepare your favorite beverage of choice (perhaps a Margarita or a zesty lime mojito) and throw open the French doors to access the pool area, which is fully fenced for privacy. The private 6' x 9' dipping pool can be heated to your liking and has a soothing waterfall. Comfortable patio furniture provides outdoor lounging options for everyone in your group. The pool area is complete with a outdoor dining set that will comfortably seat 6.brbrTHE ACCOMMODATIONS...brbrEach of the three bedrooms in THE ZESTY LIME is a suite with a private en-suite bathroom.brbr** First Master Suite: Located on the First Floor with a King bed and an en-suite bathroom with a shower and tub combo. brbr** Second Master Suite: Located on the Second Floor with a King bed and an en-suite bathroom with a spacious walk-in shower.brbr** Third Master Suite: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a walk-in shower. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room and All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Backyardbr** Private Pool with Available Pool HeatbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** Pets Considered - Max of 2 allowed and if approved an additional fee of $200 per pet will applybr** This home does not include designated parkingbr** 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.

**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$354.38

It is a 1/1 studio on the water. Comes with a washer and dryer.. Has a 10,000 BTU air conditioner. it also has access to both the Atlantic and Gulf of Mexico Waters. And parking for one vehicle.A perfect Key West day.

Charming chácara with AC in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$280.04

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 The Pinder House – where modern comfort meets historic charm in the heart of Old Town Key West! brbr brbrThis beautifully updated historic “Eyebrow” home offers the perfect blend of Key West nostalgia and vacation convenience. Located just steps from world-famous Duval Street and the Historic Seaport, The Pinder House puts you right in the middle of the island’s best dining, nightlife, and attractions — while still offering a peaceful retreat when you’re ready to relax. brbr brbrSpend your days lounging by the private heated/chilled pool, perfect for refreshing dips after a day of exploring or relaxing under the Key West sun. Start your mornings with a cup of coffee or unwind in the evenings with a cocktail on the inviting front porch — the ideal spot to watch the world of Key West go by. brbr brbrInside, the home has been thoughtfully updated with modern amenities while preserving its unique character. Enjoy relaxing living spaces, a fully equipped kitchen, and comfortable bedrooms designed for restful nights after your island adventures. brbr brbrWhether you’re exploring historic landmarks, indulging in fresh seafood, or simply soaking in the laid-back island lifestyle, The Pinder House is your ideal home base. brbr brbrBook your Key West getaway today and experience the charm, comfort, and luxury of The Pinder House! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1 (1st Floor): Queen Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (2nd Floor): Queen Bed brbr brbrLiving Room: Sofa with Pull Out Queen Bed, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely Equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Chlorine Pool (heated to ~85 degrees Nov-Apr, chilled to ~85 degrees Jun-Aug) brbr brbr- Private Outdoor Patio With Seating brbr brbr- Washer/Dryer brbr brbr- Nespresso Machine, Drip Coffee Maker, Toaster, Blender brbr brbr- Linen's and Towels Provided brbr brbr- 3 blocks to Duval Street brbr brbr- 0.7 miles to Mallory Square Sunset Pier brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 0.9 miles to Southernmost Point brbr brbr- 0.9 miles to Fort Zachary Taylor State Park Beach brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: 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 brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited 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, one exterior security camera monitors the front door. This camera is for security purposes only and does not monitor any private interior or outdoor living spaces.

The Pinder House: Historic Charm w/ Heated/Chilled Private Pool, Steps from Duval St & the Seaport

Key West, Florida, United States

Bed

Bath

Sleeps

$611.19

Welcome to The Secret Grotto — Your Luxurious Tropical Escape!brbrStep into this stunning 3,220-square-foot sanctuary nestled on nearly 5,000 square feet of lush, private paradise. This spacious Key West retreat boasts 3 oversized bedrooms, 4 full bathrooms, and an entertainer’s dream layout designed for unforgettable moments with family and friends.brbrInside, be wowed by the chef’s kitchen—gleaming with top-of-the-line Viking appliances including a 48-inch gas range, built-in steamer, wine cooler, and rich Cherry cabinetry—perfect for crafting gourmet meals or casual island snacks. The open-concept living and entertainment area flows effortlessly, ideal for relaxing or hosting lively gatherings.brbrStep outside through two grand sliding doors to your own tropical oasis. Lounge by the expansive lagoon-style pool complete with a mesmerizing grotto waterfall, or unwind on sun-kissed loungers and dine alfresco with seating for eight under the open sky. Private, fully fenced, and inviting—this backyard paradise is your personal slice of island heaven.brbrUpstairs, discover three sumptuous en-suite bedrooms designed for ultimate comfort and privacy. The primary suite pampers you with a king-size bed, cozy sitting area, smart TV, a private balcony overlooking the pool, and a spa-inspired bathroom featuring a jacuzzi tub, dual vanities, and a spacious walk-in closet.brbrTwo additional guest suites offer king and queen beds, elegant sitting areas, smart TVs, and luxurious bathrooms with walk-in closets, ensuring every guest feels right at home.brbrAdditional amenities include a two-zone HVAC system for perfect climate control, impact windows and sliding doors for tranquility and safety, plus secured off-street parking for two vehicles.brbrLocation is everything: Situated in vibrant Mid-Town Key West, you’re just minutes from pristine beaches, iconic landmarks like the Southernmost Point, Mallory Square, the buzzing 200 Block of Duval Street, and a variety of top-notch dining and nightlife options. Whether you prefer a vehicle or golf cart, everything you want is within easy reach.brbrBonus: Heat your private pool during cooler months (November 15 - May 1) for just $20 per day—perfect for year-round luxury.brbrThe Secret Grotto is more than a vacation home — it’s your personal island retreat, combining spacious elegance, upscale finishes, and unbeatable location to create a getaway you’ll want to return to again and again.

The Secret Grotto

Key West, Florida, United States

Bed

Bath

Sleeps

$785.76

Elegance. Sophistication. Perfection.brbrWelcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Key West. Located on the picturesque and coveted William Street, this extraordinary residence embodies timeless charm, architectural grace, and modern luxury — a rare gem that truly stands apart.brbrBuilt in 1866, this iconic conch-style home was originally owned by the youngest son of prominent Bahamian settlers. With each ownership, the property has been meticulously restored and thoughtfully enhanced, preserving its historic footprint while seamlessly blending in tasteful, contemporary upgrades.brbrRecognized with architectural awards and revered as one of the most exquisite homes in the Key West Historic District, the Gideon Lowe House invites guests into a world where heritage meets comfort in the most elegant fashion.brbrPROPERTY HIGHLIGHTS:brbr- 3 Bedrooms | 3.5 Bathroomsbrbr- Award-Winning Historic Homebrbr- Original Dade County Pine Throughoutbrbr- Private Pool with Waterfall & Sun Deckbrbr- Off-Street Parking (1 space)brbr- Fully Fenced Front & Rear Yardbrbr- Prime Old Town Location – 4 Blocks from Duval St.brbrINDOOR FEATURESbrbrMain Floor:brbr- Expansive sitting porch & welcoming foyerbrbr- King guest suite with walk-in closet, flat-screen TV, and luxurious en-suite bath (tub & shower)brbr- Stylish powder roombrbr- Chef’s kitchen with premium finishesbrbr- Formal dining room ideal for entertainingbrbr- Spacious living room & back entertainment loungebrbr- Lush outdoor sitting area, private pool with waterfall, sun deck & loungersbrbrSecond Floor:brbr- Dedicated laundry room & office/landing areabrbr- Lavish primary suite with king bed, flat-screen TV, oversized walk-in closetbrbr- Spa-inspired bathroom with soaking tub & walk-in showerbrbr- Private balcony with cozy seatingbrbrThird Floor:brbr- Charming third bedroom with two twin bedsbrbr- Full bathroom with walk-in showerbrbr- Generous closet spacebrbrLOCATION, LOCATION, LOCATION: brbrNestled in the desirable Historic Seaport District, this home is just steps away from the very best of Key West — world-class dining, galleries, shops, and entertainment. Only four blocks from Duval Street, yet tucked away in a quiet residential enclave, the Gideon Lowe House offers unmatched convenience with serene privacy.brbrYOUR STAY:brbrWhether you're seeking a tranquil escape or a stylish base for island adventures, this remarkable residence delivers beyond expectations. From its storied past to its curated interiors and luxurious amenities, every detail has been designed with your comfort and experience in mind.brbrDon’t miss your chance to stay in one of the most captivating homes in Key West — where history, elegance, and tropical splendor come together in perfect harmony.

The Gideon Lowe House - Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$275.79

OLD TOWN PARADISE....brParadise awaits in a cozy Truman Annex retreat. Set on a cozy lane that is off the beaten path but close enough to walk or ride your bicycle to restaurants, this unique gem offers your much needed tropical R&R!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter this sparkling, cozy abode through the front gate where a small porch with seating invites you for morning java and sultry island breezes. As you enter, a fully-equipped kitchen greets you which includes an electric stove, microwave, refrigerator, coffee maker, toaster oven, and kitchen bar area. Gather, drink and dine around the dining table for 4, then settle in the adjacent living room on your cozy sofa (pulls out as a sleeper) or cushioned chair and enjoy movies on a large flat-screen tv. Two sets of french doors welcome in the warmth and sunshine of tropical living and open to your private patio with grill and outdoor seating for 4. A convenient powder room is also located in the living area.brbrSLEEPING ARRANGEMENTS...brTravel up the stairs to two en-suite guest rooms when you're ready to rest and refresh for the next day's adventures. The primary bedroom features a king bed with dresser, small flat screen tv, a large closet for storage and hanging clothes and also includes a make-up vanity, ironing board, and iron. The private bathroom is equipped with a glass-door shower and sink cabinet with storage drawers. Open your french door to your own enchanting small terrace with two chairs and a table for quiet conversation or a date with your favorite novel. Walk down the upstairs hallway to the second bedroom which features a queen bed, flat screen tv, storage closet for hanging clothes and an additional dresser inside. The private bathroom offers a shower/tub combination and sink cabinet with storage drawers. The washer/dryer closet sits between the two bedrooms in the upstairs hallway.brbrOUTDOOR LIVING...brWalk through the living area french doors to your private outdoor area with seating for 4 and a gas grill, which is the perfect cocktail spot or for dining under the twinkling stars. Take a stroll through this attractive community which is just right around the corner from Fort Zachary Taylor State Park, Harry Truman’s Little White House and Truman Annex’s Waterfront Park. Swimming in the heated community pool is a great way to wash off the day and it's just around the corner from the unit. There is a cabana with restrooms in the pool area and plenty of lounging chairs for your sunbathing pleasure.brbrPARKING...brThis home does offer covered parking for one vehicle. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$235.38

Stunning open water views from this beautiful oceanfront home. You can enjoy quiet mornings and spectacular sunsets.brbrThe home features 2 bedrooms and 2 bathrooms. The master bedroom is equipped with a king size bed, and attached master bathroom. The guest bedroom is furnished with a queen size bed. Second bathroom can be accessed from the main living/kitchen area, as well as from the guest bedroom hallway. There is a limit of 2 pets only. brbrThis home has a fully equipped kitchen/dining area sitting for 6, as well a spacious living area, with a queen size sofa sleeper and a big screen TV. Just exit the living room, and you can enjoy spectacular views from the upstairs patio overlooking the Atlantic Ocean.br brGuests have full access to both Atlantic and Gulf from our 44 feet seawall.brbrThe downstairs area is covered, and includes a dining table and grill, where you can cook your fresh catch. There is also covered parking for 2 cars. You can explore the beautiful bay area from the home using the 2 kayaks provided. brEnjoy a day out in the sun on one of the 4 lounge chairs or watch the unique sunset from the lower level concrete patio by the water, also have a glass of wine in our TIKI HUT and enjoy the view!brbrThe neighborhood has a large community park with tennis courts, basketball, playground and a large field. It is also within walking distance to the world-famous Baby’s Coffee shop.brbrThis home is located only 10 minutes to beautiful island of Key West. Come and see what the Florida Keys have to offer!!! br

Oceanfront Paradise! (15 minutes from Duval)

Key West, Florida, United States

Bed

Bath

Sleeps

$457.6

Home of Famous Ernest Hemingway and Jimmy Buffet. Enjoy the downtown area on Duval Street where Sloppy Joe's and Captain Tony's bar are located. .Hemingway House greets thousands of visitors to experience the 6 toe cats living on the property. The Ole Light House Museum across the street is a highlight. A tropical boater's and angler's paradise boasts the best fishing and weather in the country. With tangerine sunsets glistening across the calm Atlantic and Gulf of America. An afternoon boat ride is just a perfect way to end your day. Pulling up to the docks at the famous sunset activities gathered on Mallory Square daily. Dolphin, turtle and fish sightings are possible in the turquoise waters of the keys. Lovely views from the balcony to enjoy the beautiful private outdoors. Smart TV and internet available.brbrKitchen utensils, dishes, and linens are plentiful. brbrFamily oriented community with pool/BBQ. Quiet private yard with parking. Beautiful grounds to entertain by the pool.

Charming Key West Town Home Beach/Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$390.06

PERFECT TROPICAL POOL RETREAT…brIf you've been searching for the ideal island getaway, look no further. This classic Key West jewel is precisely what your island soul has been yearning to find. This quintessential tropical nest beckons you inside its private gated entrance, where sumptuous living and sultry breezes collide in a perfect storm of blissful pleasure. Tucked into the quiet neighborhood of Midtown, you are close to pristine beaches, White Street Pier, bustling restaurants and a short bike ride to famous Old Town.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brStep inside this oasis where you are surrounded by a privacy fence that encompasses lushly landscaped front and back yards. The serene refuge of this home offers respite after a day of adventure under the southernmost sunshine. Craft your icy cocktail in the modern, fully-equipped and beautifully updated kitchen with a gas range and under counter beverage fridge, then ease onto the cozy furnishings in the adjacent living room and relax with your favorite tv show, a good book or dive into a board game together. The spacious dining room is a perfect setting to share stories over delicious cuisine with your friends and family. This home is equipped with wall mounted Roku enabled SmartTVs in every room and free WIFI. throughout. A washer/dryer is available for your convenience as well. brbrSLEEPING ARRANGEMENTS...brAll of the 4 bedrooms (to include the one in the pool house), offer smart TVs and cooling ceiling fans. The main house features a king bedroom, a queen bedroom and a twin bedroom that can convert to a king bed upon request. The king and queen rooms have desks and a laser wifi printer for those working remotely. The bedroom in the pool house offers twin beds that can also convert to a king (shown as King in photos). Both glass walk-in showers reside in the main house. brbrOUTDOOR LIVING...brThe impressive backyard oasis is a focal point of this spectacular island gem, boasting a sparkling heated pool, al fresco dining table for 10 and seating with sail shade, large propane grill, cooling outdoor shower, cafe table with seating, and pool loungers. It all adds up to an exquisite day under shaded palms and healing sunshine. Sway on the front yard hammock or hop on of of the 5 beach cruisers so you can stroll the charming lanes of Key West to the nearby Pickleball and Bocce courts!brbrPARKING...brThere is off street parking available for this home.brbrPETS...brPets are considered at this home and a pet fee is required. Please include the size/breed 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)brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).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!brbrTHIS IS YOUR HAPPY PLACE...

BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$2032.11