Vacation Home Rentals By Owner In Key West, FL

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary convenience.br brThe first floor offers a spacious living room appointed in a soothing green-and-beige palette where you can sink into a fiery coral couch flanked by a classic glass-top coffee table and oriental-style rug. Wicker and wood occasional chairs complete the scene. Open all the windows and doors to invite the soft tropical ambience inside. Or sit in air-conditioned comfort to chat with family or friends while a classic ceiling fan swirls lazily above. Use the Cable TV/DVD player, which you'll also find in the bedrooms above, to view a movie or watch a favorite show. If you're thirsty or hungry, the spotless kitchen and dining table that seats six are just steps away and waiting to be used.brbrMaybe you're ready to lounge outside on the expansive front porch, back porch, or one of the two upstairs verandas. Out back, across the terracotta brick patio, you can refresh in the swimming pool ringed by foliage and shimmering under a cloudless Key West sky. Afterwards check out the pool cabana with bedroom, bath, and inviting open-air shower. When you're ready to call it a night, you can retire to one of the two airy, comfortable bedrooms upstairs in the main house, each with full bath, or enjoy total privacy in the stand-alone cabana.br brYou've heard the term location-location-location. The home you've rented is perfectly placed for experiencing the many charms of Key West. You could start by stepping just across Caroline Street to B.O.'s Fish Wagon for lunch or dinner. As one blogger put it, the place looks like a hurricane just dumped a pile of flotsam on a street corner. In reality, B.O.'s is a favorite locals' hangout where you can order an award-winning fish sandwich as written up in The New York Times. Or, ringing the seaport just beyond B.O's, are a dozen or so eating establishments such as Raw Bar, Turtle Kraals, Schooner Wharf, and Conch Republic.brbrSince the coral island of Key West only spans fourteen short blocks of real estate from the Gulf to the Atlantic Ocean, plenty of other culinary delights-from five-star to street food vendors-are all incredibly close and accessible by foot, bike, scooter, car, pedicab, or trolley. Your choice. Many have Happy Hours from late afternoon to early evening when drinks and appetizers can be enjoyed for half price. And don't miss Mallory Square's sunset celebration where locals and visitors gather to witness and applaud as the sun sinks below the horizon. Once in a while you'll glimpse a brilliant green flash at the exact moment the sun disappears. Hang around for the party as artists and street performers entertain the crowd. Or join the throngs on Duval, browse in an art gallery, or visit the Hemingway House, Truman White House, or Key West Light House and Keeper's Quarters Museum.br brOn the other hand, maybe right now you want to move at a slower pace, on what's famously called island time. To get started, pick up libations and appetizers at Faustos Food Palace, which has been in the same location on Fleming Street since 1936. Expect to shop among writers, artists, families, locals, and visitors. While at this historic grocery store, grab a free copy of Paradise, a publication that comes out every Thursday listing upcoming special events: the music scene, movies, plays, gallery openings, and special events.brbrBring your purchases and reading material back to those comfy lounge chairs by your private heated pool. Snack, swim, sip, read. But don't forget to lather on a bit of sun screen first. If you begin to feel drowsy, let a relaxing siesta overtake you. Maybe when you wake, you'll be motivated to BBQ at your grille or cook something succulent in your fully equipped kitchen. Making the right choices in life are important and you'll know, as your time in paradise comes to a close, that renting the Kemp House has been one of those rights. If a vacation means to escape, relax, lounge, take a break, get away, this has been the absolute right place to do it.brbrThe Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. If 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.

Kemp House - in the Historic Seaport Area Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$752.42

Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom vacation home offers a tranquil oasis just steps away from the lively Duval Street and the stunning Florida Keys Beaches. brbrAs you step inside, you'll be greeted by a spacious living room, where you can unwind and plan your adventures. The fully stocked chef's kitchen, complete with a stove, oven, refrigerator, and a range of modern appliances, invites you to unleash your culinary creativity. Enjoy your meals al fresco on the balcony or gather around the dining table, savoring the flavors of the island.brbrRefresh yourself in the outdoor pool or soak in the bubbling hot tub, both perfect for unwinding after a day of exploring. Stay connected with the free WiFi, and enjoy the convenience of the in-unit washer and dryer. For entertainment, dive into the selection of books and games for kids, or simply relax in front of the smart TV with satellite or cable channels.brbrJust a 10-minute walk away, discover the vibrant Mallory Square, where you can witness the stunning sunset and immerse yourself in the local culture. With this vacation home as your base, you'll be perfectly positioned to experience the best of Key West's historic charm and natural beauty.

Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport

Key West, Florida, United States

Bed

Bath

10

Sleeps

$365.23

Summary:brbrYour Island Hideaway in the Heart of Old Town Key West with a Private PoolbrbrbrbrThe Space:brbrWelcome to Windsor Blue— Your Island Hideaway in the Heart of Old Town Key WestbrbrbrbrTucked away on charming Windsor Lane and perched atop historic Solares Hill, Windsor Blu offers the perfect blend of classic Key West character and modern comfort. This beautifully updated 2-bedroom, 2-bath retreat is your personal slice of paradise — just a short walk to Duval Street and all the best restaurants, shops, and attractions of downtown Key West.brbrbrbrThis home is well designed to share with two couples, with plenty privacy. One bedroom and one bathroom downstairs, and one bedroom and one bathroom upstairs.brbrbrbrStart your mornings with coffee on the breezy front porch surrounded by lush island greenery. Inside, you’ll find a light-filled living space with warm hardwood floors, thoughtful architectural touches, and plenty of room to relax after a day of adventure.brbrbrbrThe kitchen is fully equipped with stainless steel appliances, granite countertops, and island seating — perfect for enjoying fresh seafood or a margarita happy hour. The main floor bedroom features full-size bunk beds and exposed ceiling beams, making it ideal for families or friends. Upstairs, a cozy king suite offers privacy, spacious closets, and a modern in suite bath.brbrbrbrStep outside to your private cocktail pool, complete with a soothing waterfall, and enjoy al fresco dining under the stars. With one off-street parking space, a quiet corner lot, and tropical vibes in every direction, Windsor Blue is the ultimate home base for your next Key West getaway.

Windsor Blue Private Pool and Off Street Parking

Key West, Florida, United States

2

Bed

2

Bath

Sleeps

$2163.43

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrDOS CASITAS is the perfect property for a group of friends or a family that wants to experience Key West together in comfortable neighboring accommodations. DOS CASITAS is a cleverly named combo of two side-by-side private homes with a total of five bedrooms, five bathrooms, and an unbeatable location - half a block off Duval Street on Catherine Street. The backyards connect via a gate, allowing your group to access both homes and gather around the private pool or hot tub. Also included with the rental of DOS CASITAS is Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you have everything you'll need for the perfect Key West group vacation.brbrTHE LOCATION…brbrIf you decide to pull yourself away from these charming homes, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there are two driveways (one at each home) to accommodate two vehicles. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE LIVING AREAS & KITCHENS…brbrCASITA 1 - (aka the Duke of Catherine) was built to be the perfect vacation rental! The living area is open and spacious, feeling light and airy with a gentle tropical vibe. There is a large flat-screen Samsung Frame TV in the living room watchable from the large sofa, which pulls out to a queen sleeper for those extra guests, and the two chairs. The open floor plan seamlessly flows between the living area and the kitchen, creating even more open space and making the home feel even larger. The dining table seats 8 comfortably and the kitchen is fully equipped with every appliance and tool the chef in your group will need.brbrCASITA 2 - (aka Casa Amarilla) has a comfortable living area featuring a large flat screen TV and double French doors that open right up to the tranquil pool area. Off the living area is the fully-equipped kitchen, which includes all of the comforts of home, with plenty of counter and cabinet space. The high-top dining table located just off the kitchen seats 6 comfortably.brbrTHE OUTDOOR SPACES…brbrThe backyards of DOS CASITAS connect via a gate, so your group can easily access each property and mingle with one another.brbrCASITA 1 - The fully fenced backyard features outdoor seating for 6, a propane grill, and a spacious hot tub..brbrCASITA 2 - The fully fenced backyard features a heat optional pool, an outdoor shower, a propane grill, and an outdoor dining set with seating for 4.brbrTHE ACCOMMODATIONS...brbrCASITA 1brbr** Sunset Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Ocean Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat-screen TV, a built-in armoire, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbr** Queen-sized sleeper sofa in the living room.brbrCASITA 2 - Every bedroom in this lovely home is located on the first floor. No stairs necessary!brbr** Master Bedroom: King bed, large flat screen TV, and en suite bathroom with a walk-in shower. Pocket doors separate this bedroom from Bedroom #2.brbr** Second Bedroom: Queen bed, flat screen TV, armoire, French Doors to the pool area, and access to the shared bathroom off the living room. Pocket doors separate this bedroom from the Master Bedroom.brbr** Third Bedroom: Two Twin beds OR One King bed, flat screen TV, and access to the shared bathroom off the living room.brbrTHESE LAST KEY VACATION HOMES INCLUDE:brbr** 2 Washer & Dryersbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable 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 and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, these fully stocked homes also include, but are not limited to the amenities on this list:brbr** Fully Fenced Yardsbr** Private Pool (Heated for an Additional Fee)br** Private Hot Tubbr** 2 Propane BBQ Grillsbr** Off-Street Parking for 2 Vehiclesbr** 2 Queen Sleeper SofasbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 14 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** 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.

**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

ONLY THE BEST WILL DO…brAn exceptional opportunity to immerse yourself in island life within this renovated, classic Key West style home bordering the desirable Old Town/Casa Marina district. Enjoy a private, lush estate showcasing colorful foliage from every corner and slip inside to your breathtaking home away from home!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brA prestigious glance to this historic home greets you as you pull up to two off-street parking spaces secured by an electric gate with a spacious porch just beyond. A grand entrance into this heavenly retreat displays rich Dade County Pine, large windows inviting natural lighting in, hard wood flooring throughout and an open floor plan for the ideal family gathering. Enjoy a seating area outfitted with cozy furnishings for game night and smart TVs with streaming available. A formal dining area lies steps away with seating for 8. A cheery living room nearby includes a flat screen TV for lazy days - that's if you can resist the temptation of the stunning poolside views beyond the French doors. A fully equipped, gourmet kitchen has been updated with stainless steel appliances, granite counters and bar top seating for 2 to gather around for happy hour. A washer and dryer room is just off the living room area.brbrSLEEPING ARRANGEMENTS…brStep up to the second level to find 3 comfortable guest rooms. There are two king suites with en suite full bathrooms with soaking tubs and walk in glass showers. Steps away is another guest room with twins beds that can convert to a king upon request. The fourth bedroom lies on the third story furnished with two full beds, mini fridge and an en suite full bathroom with a shower. Enjoy a good book seated at the cozy reading nook or out on the rooftop deck in one of the loungers with incredible views. All rooms come with flat screen TV's. Another full bathroom with a shower and outdoor access is also located on the first level for guests using the downstairs sleeper sofas.brbrOUTDOOR LIVING… brExperience your very own slice of Paradise in the outdoor tropical oasis equipped with a retractable awning, an outdoor dining table for 4 and plenty of loungers for well deserved R & R. Island time doesn't get any better than unwinding in the heated, saltwater pool with a calming spillover feature. brbrPARKING...brOff street parking is offered making coming and going a breeze!brbrPETS...brPets are welcome at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. 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 only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrTIME TO UNWIND...

SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$1039.53

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThere’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has everything you’ll need to unplug and recharge your batteries, and yet you'll be within a few blocks of Key West’s premier restaurants, shopping, and attractions. This home paired with Last Key Realty's Five-Star Guest Services and Full Time Concierge staff, is the escape from reality we could all use.brbrTHE GATED COMMUNITY… brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, Truman Annex is an oasis of calm, quiet streets lined with palm trees and beautiful Floridian homes. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night. Just beyond Truman Annex is the newly constructed Truman Waterfront Park - complete with a family friendly playground area and the Key West amphitheater.brbrTHE PRIVATE POOL… brbrNo escape from reality is complete without a private pool! The entire pool area is fenced in and surrounded by lush tropical landscaping for maximum privacy. Spend your days floating in the pool, which can be heated in the cooler months, or working on your tan in the chaise lounges. When you’ve had enough fun in the sun, move the party to the covered patio, which features comfortable seating. Enjoy a poolside BBQ using the propane grill and outdoor dining options.brbrTHE LIVING AREA & KITCHEN… brbrLocated off the pool area, with its vaulted ceilings and open concept floor plan, the living area of ELEGANT ESCAPE embodies its’ name. Slide open the double doors to allow the tropical breezes to blow in while you head out to the pool. The plush sofas give you a comfortable area to get lost in a book or relax and watch the large flat screen TV. A unique addition to the living room is the wet bar, complete with a wine cooler and two refrigerated drawers. The elegant dining table has seating for six.brbrThe fully equipped chef’s kitchen features gourmet stainless steel appliances, and every tool you'll need to prepare meals from the comfort of home. There’s plenty of prep space on the kitchen island and plenty of storage in the cabinets. The half bathroom is conveniently located just off the living area.brbrTHE ACCOMMODATIONS… brbrELEGANT ESCAPE features four bedrooms – one bedroom in the main house and three bedrooms in the guest house.brbr** Master Bedroom: Located in the Main House with a King bed, a flat screen TV, a dedicated workspace, direct access to the pool area, and an en-suite bathroom with double sinks, a garden tub, and a walk-in shower.brbr** Bedroom #2: Located on the First Floor of the Guest Cottage with a Queen bed, a flat screen HD TV, mini fridge, microwave, small coffee maker, direct access to the pool area, and an en-suite bathroom with a walk-in shower.brbr** Bedroom #3: Located on the First Floor of the Guest Cottage, this open bedroom offers a Queen bed, flat screen HD TV, a couch, and direct access to the pool area. The stairs leading up to Bedroom #4 are in this Bedroom. This bedroom has access to the full bathroom in the hallway with a shower and tub combo.brbr** Bedroom #4: Located on the Second Floor of the Guest Cottage, this loft-style bedroom offers 2 Twin beds and a flat screen TV. This Bedroom is open to Bedroom #3 and has access to the full bathroom in the hallway with a shower and tub combo.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** Fully Fenced & Lushly Landscaped Private Yard br** Private Pool with available Pool Heatbr** Propane BBQ Grillbr** Covered Off-street Parking in the CarportbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** No Pets Allowed

**ELEGANT ESCAPE @ THE ANNEX** Lavish Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

3

Bath

8

Sleeps

$499.09

Three bedroom (all queens sizes beds) and three full bathroom two story home in a gated community within walking distance to several great restaurants, convenience stores, liquor and marina's with boat ramps. This property has a club house for additional rental use for parties or receptions as well as, an exercise room, and large pool. Grill located on back porch. Well stocked kitchen. Finally, all the little extra's for light packing and more time to have fun.

Tropical Key West out of the way

Key West, Florida, United States

Bed

Bath

Sleeps

$387.4

NEW PROPERTY!!!brbrExperience the best of Key West from this stunning modern island retreat, perfectly situated in the heart of Old Town’s vibrant cultural district. Built in 2019, this luxurious home blends contemporary comfort with classic Key West charm—just a short stroll from Duval Street, Fort Zachary Taylor Beach, and the Truman Waterfront Amphitheater.brbrStep inside to find a bright, open living space where the gourmet kitchen, dining area, and living room flow seamlessly together—ideal for gathering with family or friends. Oversized glass doors open to your private backyard oasis, featuring a sparkling heated pool with a cascading waterfall, sun-filled patio, and lush tropical landscaping.brbrAfter a day of exploring, retreat to spacious bedrooms with spa-inspired bathrooms, or relax on one of several covered porches to enjoy the island breeze. Every detail has been thoughtfully designed for your comfort—from hardwood floors and impact windows to custom finishes and modern furnishings throughout.brbrEnjoy off-street parking, above-flood elevation, and all the conveniences of home in a location that truly has it all—steps from Key West’s best restaurants, galleries, and nightlife, yet tucked away in a peaceful residential setting.brbrWhether you’re here for sun-soaked days or lively evenings, this property offers the perfect blend of modern luxury and authentic Key West living.

Bahama Village Sanctuary - Family & Dog Friendly

Key West, Florida, United States

Bed

Bath

Sleeps

$205.01

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 30 night minimum. This is a 2 story unit.brBedrooms: 2brBathrooms: 2brLocation: Front StbrSquare Feet: 904brParking: One assigned parking space in lotbrAmenities: Shared heated pool, TVs, Wifi, walkable to shops & restaurants downtownbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No commercial vehicles permitted in the parking lot.brPet Policy: One pet under 25 lbs. allowed with approval prior to booking and a non-refundable pet fee.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.

Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool

Key West, Florida, United States

Bed

Bath

Sleeps

$300.35

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. brbrFEATURES:brBedrooms: 4 (1 king, 1 queen, 1 queen, 2 doubles)brBathrooms: 3brLocation: Key HavenbrSquare Feet: 1804brParking: Off street parking behind gated driveway and parking along fencebrAmenities: Wifi, TVs, in-unit laundry, boat trailer parking, dock space for 1 boat, private pool, outdoor bar areabrbrbrTHINGS 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.brbrPool heating is $100 per week and must be requested in advance

Key Haven Retreat-4 bedroom 3 bath canal front home w/private pool, boat dock

Key West, Florida, United States

Bed

Bath

Sleeps

$270.53

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. brbrFEATURES:brBedrooms: 4 (1 king, 1 king, 1 queen, 1 double)brBathrooms: 3.5brLocation: Key HavenbrSquare Feet: 2097brParking: Off street parking in drivewaybrAmenities: Wifi, TVs, in-unit laundry, boat dock space, jacuzzi, enclosed patiobrbrbrTHINGS 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.

Waters Edge-Key Haven 4bedroom 3.5bath canal front home w/jacuzzi, dock space

Key West, Florida, United States

Bed

Bath

Sleeps

$1702.94

This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage. brbrLocated in Key West’s famous Old Town Historic Seaport neighborhood on two full lots, The Caroline House Estate vacation rental is comprised of two dwellings – a classic 2-story Key West Victorian house, and a hidden 1 ½ story Caribbean bungalow. brbrTHE CAROLINE HOUSE (Main Victorian House)brbrINTERIOR LAY OUT:br(Downstairs)brbrEntrance: The arts-and-crafts staircase defines the luxurious entrance to the house and leads to the 2nd floor straight ahead, where the three bedrooms in the main house are found. The expansive runs of original heart pine wood that make the interior walls of the house have been painted with absolutely brilliant tropical colors you find on the feathers of a scarlet macaw parrot. brDownstairs - left side (as you face the house): Immediately to your left of the staircase is a spacious entrance hall, fit to receive the most discerning guest. Take an immediate left again to find the fabulous Victorian sitting room with yellow-gold painted walls and styled in eclectic tropical modern fashion. Cushy floral barrel chairs surround a round bamboo and glass coffee table and prints of colorful parrots the sitting room walls.brbrA square arch leads directly to the next room, a bright red dining room furnished with an oversized round mahogany dining table and chairs. The interior decorator has perfectly placed a long mahogany side board that runs the entire length of the dining room under the sash windows. A striking bouquet of red coral is placed in the middle, and then framed with a pair of clear designer lamps topped with coral red shades to match.brbrAnother square arch flows directly from the dining room to the spacious living room where a designer sofa and chairs have been chosen for comfort and style. The large wicker sofa with nautical striped upholstery is flanked by an oversized ottoman that doubles as a lounge table. A pair of khaki print occasional chairs and an antique side table is set to the side. A large flat-screen TV is prominently placed in the living room for group enjoyment, and mounted above the TV is an impressive taxidermy of a sword fish.brbrStraight ahead is yet a third square arch that melds into the left side of the spacious kitchen, where a double set of French doors lead to the spacious deck and swimming pool. But before we consider details of the kitchen and the pool grounds let’s look at the right side of the downstairs starting from the front.brbrDownstairs – right side (as you face the house): The classic hard wood front entrance hall points all the way to the back of the house where your senses are ultimately treated to a remarkable blend of a Key West historical kitchen with contemporary culinary luxury. But first, on the way to the kitchen, you pass through a beautiful office kiosk that is set with a wooden desk large enough for two. Folk-art prints from Mario Sanchez and a rustic shutter create a charming Key West office décor. Continue through to the other end of the office to the right side of the living room, and then a final interior passage joins the living room with the kitchen.brbrThe spacious sunlit kitchen is spectacular. It encompasses most of the back of the house and feels even grander with the 12 foot high ceilings, and pendulum designer lighting that show it all off. One entire wall, from floor to ceiling, is tiled with a period correct blue and white Spanish design pattern. Against the traditional tiled wall is the contrasting modern bright white cabinets and glistening stainless steel chef’s kitchen. A large dark wooden table creates an elegant dining area for in-kitchen meals, and is joined via French doors with the back sun deck and swimming pool. Finally, at the very back of the house, off the kitchen, is a walk-in laundry room and a half-bath. There is an outdoor shower just outside the door near the laundry room and downstairs bathroom.brbrUpstairs - Back to the front door entrance of the main house, the staircase leads to the 2nd floor where you find three beautifully appointed bedrooms off the hallway. The first bedroom is the master suite. Luxuriously styled in tropical gold walls and bedding of soft shades of tropical pink and green, it’s set toward the back of the house and furnished with a traditional king size four-poster mahogany bed, upscale matching Caribbean style furnishings, original art, and a 42” flat screen TV. The completely modernized en-suite bathroom for this bedroom is done vintage style with mahogany vanity and double size walk in shower with dual shower heads.brbrNext in line down the hallway is the 2nd bedroom. Situated in the middle of the hall, it is very comfortable and offers a 27” flat screen TV. Providing two twin beds and sweetly decorated in pretty shades of coral pink and white with sea-grass headboards, it is possible to push the beds together to make a king size bed.brbrThe 3rd bedroom is at the end of the hall at the front of the main house. Shown in our slide show with a blue and white comforter, walls painted sun yellow create a striking contrast for the queen size mahogany pencil poster bed and matching wood and wicker furnishings. This bedroom also provides a 27” flat screen TV.brbrBoth the 2nd and 3rd bedrooms share a large luxury bathroom with soak tub and in-tub shower that is located at the end of the hall near the top of the stairs. brbrTHE CAROLINE COTTAGE (Caribbean Bungalow Cottage)brINTERIOR LAYOUT:brbrSet on the lot next door to the main house on the other side of the pool garden, is the 1930’s free-standing Caribbean bungalow cottage. A brass plaque on the outside announces you have arrived at ‘The Caroline Cottage.’ From the outside, it maintains it’s traditional historic cottage charm, but inside is a completely different story. brbrAs with the main house, the staircase in the cottage defines the entrance and is also the center piece for the entire interior. The architect made a dramatic statement by taking the ceiling line clear up to the roof timbers. Then the builder hand-crafted an outrageous wooden winding staircase to reach the 2nd floor sleeping loft that was made possible with the extreme vaulted ceiling. The sleeping loft is cozy and feels a bit like a secret hiding place when you’re up there. brbrThe compact yet well designed and fully equipped kitchen lines one corner of the cottage and is ideally set to serve as a preparation kitchen for entertaining guests. Beautiful tropical furnishings and soft goods fill every room. A 52” TV is placed for easy viewing throughout the main room.brbrThe master bedroom, located directly off the living room space, provides a chocolate color wicker king size bed that makes a stunning contrast against the flamingo pink walls. On the wall directly opposite the bed is a flat screen TV. The entire cottage is finished with beautiful hard wood floors that compliment the staircase. The cottage provides one full beautiful bathroom on the main floor with a bath tub and in-tub shower.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brPARKING: There is off-street parking for a maximum of 2 vehicles at The Caroline House Estate. Park in the driveway is to the left of the main house on Caroline Street, one vehicle in front of the other.brbrParking is challenging in Old Town Key West and parking meters and parking lots are relatively expensive. Since this part of the island was developed before there were cars, this should be expected. It is best to park your car, remove your valuables, lock it, and forget about it when you are here. Enjoy your location and walk or bike everywhere if possible.

The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport

Key West, Florida, United States

Bed

Bath

Sleeps

$223.25

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 EXCEPTIONSbrbrbrFEATURES:brBedrooms: 2 (1 king and 1 queen)brBathrooms: 1brLocation: Truman Annex - Shipyard CondosbrSquare Feet: 600brParking: 1 assigned parking space in gated lotbrAmenities: Wifi, TVs, in-unit laundry, patio area, shared pool, walkable to downtown shops & restaurants brbrbrTHINGS 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.

Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool

Key West, Florida, United States

Bed

Bath

Sleeps

$1509.53

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIf your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, you couldn’t ask for a more centrally-located vacation rental. The spacious interior includes five suites (each with an en-suite bathroom) and a versatile Media Room. Outside, the private backyard features a splendid, heated pool and enough space for everyone to spread out or come together for a poolside BBQ. Your stay at DUCHESS OF CATHERINE also includes Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you’ll feel like royalty.brbrTHE LOCATION…brbrIf you decide to pull yourself away from this beautiful home, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there is off-street parking in the driveway for one vehicle if you decide to bring one. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE LIVING AREA & KITCHEN…brbrDUCHESS OF CATHERINE was designed and furnished with comfort in mind. The open living area is ideal for gearing up to head out on the town or for unwinding after a day full of adventure on the water. The spacious living room has a large flat-screen Samsung Frame TV that can be enjoyed from the two plush sofas or chairs. The fully equipped kitchen is next to the living room, with every appliance and tool needed to prepare a meal at home. The extra-large dining table seats 10 and there’s additional seating at the kitchen bar.brbrTHE PRIVATE POOL…brbrNo royal vacation is complete without a private pool to spend your days relaxing in. The fully fenced private pool area gets equal amounts of sun and shade throughout the day. Your private saltwater pool can be heated in the cooler months upon request. Kick back poolside in the chaise lounges or gather the group for an outdoor BBQ using the propane grill and outdoor dining set.brbrTHE ACCOMMODATIONS…brbr** Florida Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Paddleboard Suite: Located on the First Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Media Room: Located on the First Floor with a sofa that pulls out into a Queen to accommodate extra guests and a flat-screen TV.brbr** Whale Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Flamingo Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Aviary Suite: Located on the Second Floor with a King bed, a flat-screen TV, a closet, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable 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 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 Yardbr** Private Saltwater Pool (with Pool Heat for $30/day)br** Propane BBQ Grillbr** Off-Street Parking for 1 Vehiclebr** Queen Sleeper SofabrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 14 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** 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.

**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

6

Bed

5

Bath

14

Sleeps

$2831.25

Discover the beauty of Key West from this spacious property. The property is perfect for hosting conventions.brThis would be an excellent property to use as a screen for an action movie.brThere is lots of free parking available and it is right next to Bernstein Park.

Serene 3-bedroom house with AC in charming Key West + private, small house

Key West, Florida, United States

3

Bed

1

Bath

29

Sleeps

$198.02

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 Castaway Cove! Nestled in the vibrant New Town area of Key West, Castaway Cove is your perfect home away from home! brbr brbrThis charming 2BR townhome offers a blend of comfort, convenience, and coastal charm, making it an ideal getaway for families, friends, or couples. Castaway Cove offers a spacious and tastefully decorated living area with comfortable seating and a flat-screen TV. Fully equipped kitchen with modern appliances, perfect for whipping up your favorite meals, as well as a cozy dining area for enjoying meals together. There are two well-appointed bedrooms with plush bedding and ample storage. Private patio with outdoor seating and a BBQ grill, ideal for al fresco dining and relaxing. Shared pool just steps away, perfect for cooling off and soaking up the Florida sun. Kayaks available for exploring the beautiful waters of Key West. Castaway Cove is situated in the heart of New Town, providing easy access to the island’s best beaches, an array of restaurants, cafes, and bars, local shops and popular attractions like the Key West Butterfly and Nature Conservatory, the Ernest Hemingway Home and Museum, and the vibrant nightlife of Duval Street. Whether you're seeking adventure on the water, relaxation by the pool, or exploring the local culture, Castaway Cove offers the perfect base for your Key West vacation. Book your stay today and experience the charm and beauty of this tropical paradise! brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1: Queen Bed (adjustable), Smart TV (no cable/satellite available) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite available) brbr brbrLiving Room: Sofa w/ Two Recliners, Chair, Smart TV (no cable/satellite available) brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool (heated and chilled) brbr brbr- Private Patio brbr brbr- Propane BBQ Grill brbr brbr- Keurig, Drip Coffee Maker, Toaster, Blender brbr brbr- Two Parking Spaces Included brbr brbr- Linens and towels provided brbr brbr- 2.2 miles to Smathers Beach brbr brbr- 2.2 miles to Duval Street brbr brbr- 2.3 miles to Historic Seaport brbr brbr- 2.4 miles to Southernmost Point brbr brbr- 2.8 miles to Mallory Square Sunset Pier brbr brbr- 3.0 miles to Fort Zachary Taylor State Park 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.

Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!

Key West, Florida, United States

Bed

Bath

Sleeps

$244.39

28 DAY MINIMUM RENTALbrbrThis bright and sunny cottage is situated on a quiet residential street. Guests can walk to the nearby beaches, White Street shops, and enjoy the sunny pool, hot tub and patio space.brbrA large open kitchen, skylights, light tile floors and french doors leading from the living room & both the bedrooms to the pool area create a real indoor/outdoor living experience. The living room is spacious & comfortable with bright tropical colors with a small lounging corner where you can relax in the overstuffed chaise, read a good book, take a nap, all while gazing out to the pool and patio. Several new upgrades have been added by the owners including a new ductless air conditioner to cool or heat the living area.brbrThe master bedroom sits to the rear of the property with french doors to a private patio space complete with the new 6-person hot tub. It's your own outdoor spa! The second bedroom is on the front of the house adjacent to the living room with French doors leading out to the pool. Bedding: 2 kings, 1 sleeper sofa.

South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub

Key West, Florida, United States

Bed

Bath

Sleeps

$492.64

28 DAY MINIMUM RENTALbrbrReynolds Retreat is quintessential Key West living. Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience.brbrThe wide stone patio surrounded by a white picket fence is the perfect spot for lounging with morning coffee or a cold afternoon drink. As you enter the home, buttery Dade County pine walls and floors flank an unobstructed view all the way into the backyard. To the right there is a bedroom with lovely transom windows and a dramatic, gray and green marble bathroom with a sunken tub. Just across the hall is a quaint sitting room.brbrThe living area is open-concept, with high ceilings and unobstructed views of the renovated kitchen, providing a perfect place to unwind and entertain. Walls of floor-to-ceiling sliding doors open to reveal a sparkling, cerulean, lagoon-style heat optional swimming pool. Another bedroom lies within the pool’s cabana, giving guests plenty of privacy and space.brbrThe exposed walls in the upstairs main suite are stained a soothing olive, and the bathroom is tiled in rustic, natural stone. Reynolds Retreat is a relaxing oasis just far enough from the bustle of Duval Street. It’s the perfect spot to make your home-away-from-home in paradise.brbrBedding: 3 QueenbrOn Street Parking

Reynolds Retreat - A Great Monthly Getaway

Key West, Florida, United States

Bed

Bath

Sleeps

$1977.57