Home Vacation Rentals By Owner In Key West, FL

Showing 340 Of 2059 Vacation Rentals
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Exceptional(10)

$994.08

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Private Vacation Home

GARDEN HIDEAWAY ~ Gorgeous 4 BR, 3 BA w/private heated pool and lush gardens!

Key West, Florida, United States

PARADISE AWAITS...brThis charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden Hideaway is situated on an oversized lot which is filled with lush foliage that creates a luxurious garden oasis.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brThere are four bedrooms in this sprawling home with a great layout that allows privacy. The spacious first floor primary suite has windows lining the sleeping space as well as French doors so you have wonderful views and access to the gardens and pool, furnished with a king bed and en suite bath to include a shower with a glass block enclosure and a soaker tub. The next bedroom acts a a suite with a small adjoining bedroom with a trundle bunk bed and en suite bathroom. An additional main floor bedroom has a Queen bed and French Doors that open to the outdoor patio. The fourth bedroom is located up the spiral staircase and comes with a queen size bed with a memory foam topper. There are two additional full bathrooms with showers on the first level of the home. All bedrooms come with TVs and plush bedding.brbrAMENITIES...brStep through the French doors to an expansive entry way which leads you to the heart of the home. The Great Room is open to the kitchen which makes this the perfect spot for entertaining. The living room has plenty of seating, a Sonos speaker system, smart flat screen TV as well as several windows overlooking the landscaped yard. Top notch dining furniture is available at the indoor table for 8 or out on the patio. The newly renovated kitchen has new dishware, cookware, kitchen utensils, and flatware as well as stainless appliances and is fully equipped. Fresh new cabinets and quartz countertops give the space a crisp, clean look. The home is glowing with recent updates to include new indoor/outdoor furnishings with upscale finishings.brbrOUTDOOR LIVING...brLush landscaping with automatic evening lighting creates an oasis that relaxes you once you step through the front gate. Stroll along one of the many brick pathways which travel throughout the property. Sit on one of the various decks, covered porches or seating areas with custom cushions, overlooking the gardens. Enjoy outdoor dining with your family with an unparalleled custom outdoor kitchen to include granite countertops housing a Coyote BBQ grill, 2 burner stove, ice maker, refrigerator, farm sink, stainless steel drawers and trash bin. Enjoy outdoor fans, lighting and a smart TV in this inviting space with a Solo fire pit for use on the occasional cool evenings. Whether swimming in the pool or lounging with a book, relaxation awaits. brbrPETS...brThis home is pet-friendly 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. 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 min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
Bed 4

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Bath 3

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Sleep 10

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Exceptional(1)

$343.86

/ Nightly
Private Vacation Home

LONE PALM COTTAGE ~ 3 BR, 2.5 Ba Home w/ 2 Cottages, Pool & Parking!

Key West, Florida, United States

OLD TOWN AMBIENCE....brLuxury Old Town Key West Monthly Rental – Private Heated Pool, Quiet Lane, Off-Street Parking, Sleeps 4-6 – 28-Night Minimum Stay. Nestled on one of Old Town Key West’s most peaceful lanes, Lone Palm Cottage captures the essence of Key West living with refined comfort and privacy. Lush tropical garden views, swaying palms, and a charming porch with graceful scrollwork set the tone for this private Old Town home. The property includes a main house and two guest cabanas, offering separate sleeping quarters and complete privacy — perfect for discerning guests or extended stays. At its heart lies a 12’ x 18’ saltwater pool with a soothing fountain, surrounded by orchids and palms. Inside, historic Dade Pine craftsmanship meets modern luxury, featuring a chef’s kitchen with Wüsthof, Le Creuset, and Revere cookware, a high-speed Fiber Optic Wi-Fi workspace, and an on-premises washer and dryer. Just a short walk to Duval Street, fine dining, and the seaport, Lone Palm Cottage delivers authentic Key West charm and boutique exclusivity — a serene retreat for travelers seeking privacy, sophistication, and a genuine connection to the island’s timeless allure. There is a Ring doorbell located on the front door of this home for security purposes.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES....brInside, the airy living space welcomes you with vaulted ceilings, classic Dade Pine walls, and sunlit windows that create an atmosphere of relaxed sophistication. French doors open to the outdoor terrace, blurring the line between indoor comfort and open-air leisure. The chef’s kitchen, appointed with Wüsthof, Le Creuset, and Revere cookware, offers both beauty and function — complete with a pass-through for effortless entertaining or alfresco dining. Designed with balance and flow in mind, Lone Palm Cottage combines historic craftsmanship with modern elegance, creating a calm, inviting environment that reflects the best of Key West living.brbrSLEEPING ARRANGEMENTS...brLone Palm Cottage is designed to provide both comfort and privacy, making it ideal for couples, extended families, or guests traveling together who appreciate their own space. The primary suite in the main house features a queen bed, an en-suite bath with a double-entry shower, and a dedicated workspace with high-speed Fiber Optic Wi-Fi, perfect for quiet mornings or catching up on work in comfort. Each of the two guest cabanas offers a queen bed and private entrance, creating a boutique-style experience that allows everyone to unwind at their own pace. One cabana includes a full bath, while the other features a half bath with a vanity sink, offering flexibility without sacrificing elegance. Thoughtfully arranged around the garden and pool area, these accommodations blend Old Town charm with modern sophistication, ensuring every guest enjoys a restful and rejuvenating stay.brbrOUTDOOR LIVING...brOutdoors, Lone Palm Cottage transforms into a private retreat designed for relaxation and indulgence. The saltwater pool, which can be heated or cooled depending on the season, is surrounded by lush palms and orchids that sway softly in the tropical breeze. After a refreshing swim or an afternoon in the sun, the outdoor shower offers a secluded, open-air escape — a refreshing, sensory experience that captures the essence of Key West living. The dining terrace and lounge area invite unhurried evenings for conversation, dinner, or quiet moments beneath the stars. Two beach cruiser bicycles are provided for leisurely rides through Old Town’s charming streets and waterfront paths — a signature pleasure of Key West living. Every element of this outdoor space is crafted to extend the home’s quiet sophistication and timeless charm into the open air — an intimate setting where comfort meets understated elegance.brbrPETS...brThis is not a pet-friendly home.brbrPARKING...brThis home offers off street parking for 1 vehicle.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. 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).brbrPRISTINE PRIVACY IN PARADISE...
Bed 3

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Bath 2

Bath

Sleep 6

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$174.39

/ Nightly
Private Vacation Home

Monthly rental-Old town one level home w/ shared, heated pool, parking, a/c,heat

Key West, Florida, United States

*Key West only allows us to rent the home for 28 nights minimum, so I won't be able to respond to inquiries for rentals shorter than that time frame* Owner prefers the calendar month starting the 1st and last day of month. Exceptions can sometimes be made. This is a 1 level home with only 3 stairs up to the home. It has 1 bedroom 1 bath with a walk-in shower. It is a single family home that is 800 sq. ft., located just 7 blocks to Duval and a 10 minute walk to Higgs beach. This home is in a quiet community and shares a beautiful courtyard area with 11 homes surrounding a large heated swimming pool and is ideally located within easy walking distance to the beach, world famous Duval Street, shopping, museums and restaurants. We ask that only guests that have great prior past reviews on file request to book the home. You will love the heated, shared pool and beautiful courtyard along with the side deck and front porch. You will love being close to everything including the grocery store, coffee, beach and more. It has a Walk-in shower. 1 designated Parking space. Shared heated pool. Home has a/c and heat- 2 mini splits. All Utilities including internet and basic cable. There is 1 queen bed and 1 pullout double bed in the front living room. Great for 2 people as the bathroom is in the bedroom so if you have guests they will have to enter your bedroom to get to the bathroom. Located on Catherine St. at Watson. 1 designated parking space in front of home with room for a motorcycle too. The other side of the street is open parking for anybody to use. No laundry on site. There are 3 laundry mats all within a few blocks and one will pick up and redeliver your clean laundry. This is not a home for parties and you can only have your designated registered guests staying overnight at the home and a couple others maximum at the pool as the pool is shared and its quiet. This home has a front porch along with a large side deck overlooking the garden. There is also seating at the pool. It has very high ceilings so it feels larger than it would seem. The bedroom has a door to the addition on the back of the home and then french doors to the deck and a door to get to the pool. No smoking allowed inside or at the pool. The home is from 1906 and has original flooring, windows, bath, and kitchen cabinets so it's not in perfect shape and you can tell those things are older. The addition in the back of the home is new, some windows in the kitchen storage area and bath are new, and the deck is new . It may be considered by some to need some updating such as the kitchen, baths, floors. The floors are original. The bath tile is original. The kitchen has new cabinet doors (refaced). Owner allergic to cats. Small dogs under $20 pounds are ok with $300 non refundable pet cleaning fee. No cats as owner is allergic. Dogs are not allowed to be off leash anywhere outside In the yard or in the courtyard where the pool is. The yard and the courtyard all run together with no fence so your pet would need to always be on a leash in the front yard or side yard or back yard. The neighbor next door has a small dog. Located within blocks of beaches, shops, restaurants, and museums! If you're here for the sand and sun, several local beaches are located less than a mile from your rental. Cast a line, people-watch, or enjoy the views from the Edward B. Knight Pier or Higgs Beach Pier, or head over to Duval Street for the area's best restaurants, bars, and boutiques. Begin your day with a refreshing dip in the beautiful, shared swimming pool, enjoy a meal out by the furnished pool and then kick back and watch the world go by from the front porch.brTravel insurance is recommended, as we cannot change our cancellation policy.
Bed 1

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Bath 1

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Sleep 3

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Exceptional(46)

$1212.41

/ Nightly
Private Vacation Home

Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool

Key West, Florida, United States

A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select private homes to the public. A total renovation created a stunning one-of-a-kind tropical water pavilion by bridging two cottages with a pool, spacious deck and lushly landscaped garden. The pool is made both mysterious and fantasy-like with beautiful glistening stones and a giant frangipani tree which drapes the pool. Just a few blocks from Mallory Square, steps from grocery shopping, excellent restaurants, popular clubs, the Historic Seaport, and tropical shops makes this one of the most requested and convenient accommodations in Key West. We are so pleased to offer it as one of the more unique properties available in Old Town.brbrThe Pavilion Villa vacation rental home was re-designed to create a spectacular indoor and outdoor multi-level living space which is both elegant and playful. Enter the main cottage from the street side, and you`re immediately reminded you`re on an island by delightful tropical reef carpeting that adorably covers a charming historic staircase leading to the 2nd floor sleeping loft. Here you find a 1 ½ story dwelling which houses the living room, kitchen, three bedrooms, and a full bath with a beautiful indoor/outdoor shower room.brbrThe inventive layout of the main historic cottage maximizes the use of available space, using every nook and cranny to offer something both functional and beautiful. Immediately inside the front door to your left, is the first bedroom with two twin beds that can be put together to make a king bed on request. Straight ahead of the front door is the small scale historic stair case which leads to a loft-style bedroom. This bedroom provides a queen size bed, and has an added feature of a roof-top balcony that overlooks the pool. Back downstairs is one more bedroom, with a king size bed, and an artistic Caribbean blue bathroom with a sunken tub and elaborately tiled large private indoor/outdoor garden shower.brbrThe dining room, kitchen, and beautifully furnished living room are towards the back of the main cottage, and are linked to the pool and deck through double sets of French doors. An outdoor dining table and chairs set just outside the doors serve to extend the living area to the outdoors to the pool and deck area which draw you to the second two-story cottage which is on the opposite side of the pool. Once on the deck pavilion, it is almost impossible to proceed to the back cottage without stopping to dip your toe in the pool, and take in the beauty of the garden. The private spacious deck has plenty of room for sunning and lounging. A second bathroom in the outdoor garden area, consisting of a sink and commode room, and tiled shower room, makes indoor/outdoor living fun and convenient. The main cottage also provides a walk-in laundry room with washer / dryer.brbrWalk the deck past the pool to reach the second cottage at the back of this unique paradise pavilion. The back cottage has 2 full stories with the first floor set up as a sleeping and lounging area. There is also a large kitchenette and breakfast bar for convenience. The second floor has master bedroom with king size bed and full bathroom, and a spacious balcony which overlooks the pool and looks back towards the front cottage.brbrThe design of the Pavilion Villa Key West vacation rental makes it ideal for family groups or groups of friends. The pavilion-style plan provides two private buildings which are adjoined with a spacious outdoor living room for all to gather. It should be considered as an ideal location for a wedding party to reside, but not to stage the wedding. At the same time, the intimacy created by the garden pool pavilion make this unique home a wonderful location for a couple or a smaller group who want privacy and room to spread out.brbrThis home is offered as an exclusive vacation rental in the most requested location in Key West. The property will not tolerate smoking inside.brbrIf you love this villa but need to sleep more people, you can rent it with the two bedroom cottage Down Island Digs. You can combine a rental of both properties and sleep up to 12 by renting the Island Rendezvous vacation compoundbrbrbrFront Cottage:brbrbrDownstairs - 1 king size bed, 2 twin beds (can be pushed together to make a king)brbrUpstairs - 1 queen size bedbrbrbrBack Cottage:brbrbrDownstairs - 1 queen sleeper sofabrbrUpstairs - 1 king size bed (master bedroom)brbrbrbrAmenities: Private Swimming pool with exotic landscaping, roof top deck, full pool bath, fully fenced and private, fully equipped kitchen, 2nd service kitchen, unique separate living areas, color cable TV`s, DVD, stereo, a/c, telephone, propane grill. Laundry room with washer / dryer. All linens and towels provided, parking, just 3.5 streets from Mallory Square.brbrActivities: Around the corner you`ll find fantastic retail stores, wonderful famous restaurants such as Margaritaville, and unique local museums such as the Custom House, Mallory Square Sunset Celebration and the Hemmingway House where Ernest Hemingway lived. Sailing, boating, diving, museums, nightlife is close by.brbrArea: Downtown Old Town Historic Key West. Just one-half block off Duval Street. Walk to all Old Town Key West features. Great restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Ship Wreck Museum. 10 minute stroll from the famous Sunset Celebration at Mallory Square.brbrRestrictions: Smoke free house. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brPARKING: There is one (1) parking space only for Pavilion Villa, but please note it is NOT the driveway to the right of the house. The parking space is kiddy corner, and across the street from the house. With your back to the house, look across the street and to your right, to see the lot.brbrPark in the space in the lot marked with the parking sign on the fence that reads ‘510 Bahama.` DO NOT park in ‘Fausto’s Fine Foods’ parking lot directly across Bahama St. There is a parking attendant who watches nearly 24 hours a day, and if you park there you will be ticketed or towed.brbrShort Driveway in front of the House: There is a short driveway in the front to the right side of the house, between this property at 510 Bahama St., and the cottage next door at 508 Bahama St. Notice: This space is for loading and unloading only. This space is too short to park a car in, and if your car hangs out even slightly over the sidewalk, you will most certainly be given a ticket by the diligent parking officers that patrol downtown Old Town Key West. Do not block the gates, or you will be in violation of fire safety regulations.brbrParking is challenging in Old Town Key West and parking meters and parking lots are relatively expensive. We are sorry for any inconvenience, but 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.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(67)

$1739.32

/ Nightly
Private Vacation Home

**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrGet the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a massive exterior living area, including outdoor dining, your own gym, a private saltwater pool and poolside lounge. The inside maximizes the best of togetherness and privacy: each bedroom is complete with an en-suite bathroom and flat screen TV. This special beach mansion, combined with Last Key Realty's Five-Star Guest Services, will make your stay in Key West a guaranteed success for the entire group.brbrLooking for a longer stay at this beautiful beach mansion Book this home as BEAUTY OF THE BEACH at a discounted rate as a monthly rental.brbrTHE LOCATION...brbrThe Beachside neighborhood of Key West is a quiet, mostly residential neighborhood on the southern side of the island. Just a block from the west end of Smathers Beach off Atlantic Blvd, and just down the street from Higgs Beach, BELLE OF THE BEACH is a dream for beach-lovers who prefer to pack their coolers and towels and walk the few steps down to the sand and water. Watch the sunset from Smathers Beach or the White Street Pier just around the corner. Take the short stroll to Salute! for a beachside meal, or bike ride (or a quick Uber) down to Duval Street or the Historic Seaport for the most popular Key West attractions. brbrTHE INTERIOR LIVING AREA & KITCHEN...brbrThe interior living area of this home is just one part of the available living space, but offers plenty of room for the whole group. The sectional sofas, which also pull out to Queen sleeper sofas, sit in front of a large flat screen Smart TV. Off the living area is the dining area with space for 8 diners, plus additional seating at the kitchen bar. The kitchen is upgraded with state of the art appliances and tools, including a Kuerig coffee maker.brbrTHE EXTERIOR LIVING AREA & SALTWATER POOL…brbrA major perk of this stilted home is the massive outdoor area created under the house. A full outdoor living area with luxurious lounge furniture and outdoor dining tables galore sit in the shade of your mansion. Beside the house is a private saltwater heat-optional pool with plenty of chaise lounges for relaxing poolside. There is also a personal gym with various equipment pieces for your use (but if the only exercise you envision is drink bicep curls, no judgement here!)brbrTHE ACCOMMODATIONS...brbr** Nautical Suite: Located on the First Floor with a King bed and an en-suite bathroom.brbr** Floral Suite: Located on the First Floor with Two Twins OR One King and an en-suite bathroom.brbr** Sea Life Suite: Located on the First Floor with Two Twins OR One King and an en-suite bathroom.brbr** Beachy Suite: Located on the First Floor with Two Twins OR One King and an en-suite bathroom.brbr** Music Suite: Located on the Second Floor with Two Twins OR One King and an en-suite bathroom.brbr** Coral Suite: Located on the Second Floor with a King bed and an en-suite bathroom.brbr*The Second Floor has a landing with a mini fridge and a balcony.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & 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 Saltwater Pool with available Pool Heatbr** Off-Street Covered Parking in Drivewaybr** Propane BBQ Grillbr** Fitness EquipmentbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 16 adults (2 Queen sleeper sofas)br** 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.
Bed 8

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Bath 6

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Sleep 16

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Exceptional(40)

$1993.28

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Private Vacation Home

Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16

Key West, Florida, United States

Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once historic and exotic. If you`ve ever had the opportunity to stroll the residential streets of the famous Key West Historic Seaport neighborhood, you have experienced first-hand the type of incredible architectural history embodied in this authentic turn of the 19th Century property. The location of this estate property is where you`ll find some of the most iconic destinations on the island.brbrDisplaying an abundance of elegant Victorian design, artisan ship carpenters milled elaborate gingerbread trim that the front of the 7 BR 5.5 BA Classic Key West Estate home. Deep porches with turned columns grace the entire width of the first and second floor porches. Beautiful stained glass transom windows top symmetrically set French doors. Oversized windows surround the home to invite in the light and tropical breezes. A beautiful pool-side pied-a-terre, in the private back yard, provides the perfect touch of fantasy. The quintessential white picket fence with capital topped posts gracefully surrounds the front yard to complete the perfect picture of opulence. brbrInterior Layout: Throughout the years, the interior of this home has mostly, retained its original layout. Many of the walls in the house feature the revered heart pinewood planks used to build this home in the late 1800’s. During renovations in the 1970’s, much of this long extinct pinewood, was meticulously hand-sanded by craftsman to reveal its natural warm glow.brbrThroughout the Classic Key West Estate, the historic rooms are furnished and decorated with up-scale tropical furniture and pleasing artwork. Featured on one living room wall, is a commissioned historiography art piece that depicts the timeline of this estate. It was researched and created by local professional historian Sharon Wells.brbrA classic 1800’s Federal style center-hall makes an impressive entrance statement. Step inside and the wide 1st floor hallway leads to the back of the house. Stately rooms with 12- foot ceilings line both sides of the house. The wooden banister staircase was intricately carved by early artisans. It provides the visual center point of the first floor.brbrRight side (facing the front of the house): On the front right side of the staircase is the spacious living / media room. It is nicely furnished in light tropical colors with traditional wood and wicker furnishings. A 50-inch TV provides the focal point for shared media entertainment.brbrThe living / media room is open to the dining room via an expansive wooden archway. The dining room is nicely staged for group dining. A single door at the back wall of the dining room leads to the upscale kitchen.brbrThe kitchen was stylishly renovated with luxury upgrades. Walls are painted a dramatic blue, in striking contrast with the bright white cabinets, stainless steel appliances, and earth tone granite counter tops. brbrThe kitchen is located at the back of the house. This is ideal for enjoying the indoor / outdoor Key West lifestyle. Two sets of French doors, at the back corner of the kitchen, lead to the pool and deck area.brbrBedroom One: Returning to the front of the house, the first room on the left is bedroom one. Nicely decorated to double as an office / den, it has a Murphy bed on one wall. The bed makes up as a comfortable queen size bed. brbrBedroom Two: Walking toward the back of the house, the next door on the left is bedroom two. This bedroom is authentically furnished and includes a metal king-size bed, and an antique wooden dresser and armoire. This bedroom also provides an en-suite bathroom.brbrIn contrast with the bedroom, the en-suite bathroom is a modernistic design. It is decorated in white and fitted with a double wooden vanity topped with chic composite countertops. The shower is oversized with frameless glass doors. Contrasting black bathroom fixtures add elegance to the room.brbrBack out to the hallway, the last room on the downstairs left is a half-bath with a sink, commode, and mirror. Conveniently located near the back yard pool it serves as the pool bath.brbrPool and Deck: The most direct path to reach the back yard and swimming pool, is through the kitchen. At the back corn wall of the kitchen double sets of French doors open to the deck.brbrThe backyard deck is set up as an outdoor lounging and dining area. A dining table with chairs are placed under a covered porch. An awning extension adds protection from the rain. The outdoor dining table is positioned near the kitchen making it easy to serve and entertain outside. For poolside media enjoyment, a flat screen TV is placed on the exterior wall above the table.brbrStudio Cottage – Bedroom Three: A bonus feature of this estate property is the upscale free-standing studio cottage, with a full bathroom and kitchenette. It provides two full-size (double) beds that are positioned to catch a view of the pool.brbrSituated across the back deck from the main house, it offers privacy from the main house. Décor is elegant with pinewood walls and open-beamed ceilings.brbrReturning to the front of the house, we ascend the banister staircase to the 2nd floor. The landing leads to an impressive and dramatic hallway.brbrAt the front and back of the 2nd floor, exterior doors lead to covered porches. The front door connects with the 2nd floor covered front porch, that spans the width of the house. From up here enjoy a view of beautiful Fleming Street below.brbrAt the back of the house, a door leads to the upstairs covered back porch. From here enjoy a view of the neighborhood rooftops and the pool-garden below. brbrThere four bedrooms and two bathrooms upstairs. All four bedrooms are spacious and feature 10+ foot ceilings. Each upstairs bedroom is uniquely decorated yet integrated in design with the other bedrooms. All four bedrooms provide a king size bed, dresser, bedside tables, and reading lamps.brbrThe right side of the upstairs has two spacious bedrooms and one bathroom. During an early renovation, Key West craftsmen meticulously restored the original pinewood walls on the upstairs right side of the house. The warm hand-rubbed wood honors the historic authenticity of the house.brbrBedroom Four: Apart from the beauty of the wood walls and high ceilings, bedroom four has windows on two walls that invite in the natural light. The fourth bedroom offers a king-size. It also has a nice view of the covered front porch.brbrBedroom Five (with en-suite bathroom): The fifth bedroom five is the next room down. It can be accessed from the hallway, or through double French doors which connect to bedroom four. You may have to flip a coin to see who gets bedroom five. Bedroom five is prominently furnished with a dark-wood canopy king-size bed and features a beautiful historic en-suite spa-bathroom.brbrEn-suite Spa Bathroom: The Colonial-Caribbean design of this special spa bathroom creates an aire of island romance. A soaring ceiling adds to the spacious feeling and adds a dramatic flair. There is an oversize shower in one corner. A double white wood vanity sink is topped with a large antique mirror that bounces around the light. An upholstered chaise, set against the bare wood walls, give this special bathroom an exotic feel. brbrIn elegant contrast to the bare wood walls on the right side of the upstairs, all bedroom walls on the left side are painted a soft yellow. Painted antique planks create a light backdrop to show off dark wood and wicker beds and pleasing artwork.brbrBedroom Six: Returning to the front of the house, bedroom six is in the upstairs left corner. As a corner bedroom, there are two exterior walls with four large sash windows that invite in the sunlight. Bedroom six provides a king-size bed.brbrBedroom Seven (with en-suite bathroom): Back to the hall and past the stairs, bedroom seven is the next in line. also provides a king-size bed. While there is only one exterior wall in bedroom seven, oversized windows assure plenty of natural light. Bedroom seven connects with a full en-suite bathroom, with a second door that leads to the hallway.brbrSecond Upstairs Bathroom: The last room at the end hallway, on the left, is a full bathroom with shower. Bedroom four and six, at the front of the house, share this bathroom.brbrGrounds: The property grounds are fenced in the front and back for privacy. The back yard is decked creating a wonderful place for private entertaining complete with swimming pool, and an upstairs verandah creates a covered loggia. Beautiful palm trees and foliage create a romantic tropical setting. The front of the home has beautiful curb appeal with large front porches on the first and second floor that overlook the estate neighborhood.brbrNote: If your group grows, or if you just want more room to spread out, rent this home with a private Caribbean Guest House. The combination of the two houses is available to rent as the 10 BR 7.5 BA Old Town Caribbean Estate. brbrActivities: Walk to all old town features, no need for a car. Just 3 1/2 streets to Duval St., close to Key West Mallory Square Sunset Celebration, and a few short streets from Historic Seaport and retailers (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Conveniently located to gourmet grocery shopping with excellent wine selection. Close to shopping, art galleries, and a variety of restaurants, coffee shops. Close to the beach.brbrRestrictions: While this property is ideal for families and groups, it is not suitable for staging loud parties. Smoking permitted outside only. No pets please. Guests under 25 years of age must be accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
Bed 7

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Sleep 16

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Exceptional(14)

$2022.43

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Private Vacation Home

Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8

Key West, Florida, United States

OVERVIEWbrThe 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The house can accommodate eight (8) guests - two (2) queen beds, two (2) full beds, and one (1) sectional with a queen sleeper. The house has a wrap-around upper balcony, and a wrap-around porch, overlooking the pool, sun deck, and Thomas Street.brbrThe design of this property lends itself perfectly to small gatherings of families and friends.brbrThe house is completely furnished with linens, towels, has a full kitchen (all cooking and eating utensils), Corian countertops, maple cabinets, Samsung side-by-side refrigerator (ice maker, serve thru water/ice dispenser), GE microwave, Whirlpool dishwasher, full size washer and dryer, central A/C (zoned Rheems, 3 + 3 tons), 6 ceiling fans, Starlink high speed wi-fi internet access, streaming internet TV, (4) SMART HDTVs ((2) 40 Samsung SMART HDTVs, (1) 40 Sony SMART HDTV, and (1) 32 Samsung SMART HDTV.brbrMASTER BEDROOMbrThe master bedroom has a queen size bed, clothes closet, dresser, 52 Hunter ceiling fan, and a 40 Samsung SMART HDTV.brbrSECOND BEDROOMbrThe second bedroom has a full size bed, a clothes closet, a dresser, and a 52 Hunter ceiling fan.brbrTHIRD BEDROOMbrThe third bedroom has one (1) queen bed, a dresser, and a 52 Hunter ceiling fan, and a 32 Samsung SMART HDTV.brbrbrFOURTH BEDROOMbrThe fourth bedroom has one (1) full bed, a dresser, a 52' Hunter ceiling fan, and a 40 Sony SMART HDTV.brbrCOMMON ELEMENTSbrThe five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is secured wireless internet access, and CCTV (garden (2), pools (2), and property perimeters (3)). The design of the property lends itself perfectly for small gatherings with friends and family.brbrLANDSCAPINGbrThe landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways. brbrEXCELLENT LOCATIONbrThe house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the center of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.brbrCHICKENS & ROOSTERSbrThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!brbrCRITTERSbrAlso, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.
Bed 4

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Bath 2

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$272.01

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Private Vacation Home

Waterfront Key West Oasis w/ Float Dock!

Key West, Florida, United States

A taste of the tropics awaits at this gorgeous 3-bedroom, 2.5-bath vacation rental! Make a splash off the dock, soak in the swim spa, or explore on your time via the provided bikes and kayaks. Inside, discover space for the whole family, along with furnishings freshly renovated in 2021. When adventure calls, choose to visit local beaches, wander Old Town, or launch a boat into the Gulf of Mexico. Come home to a refreshing rinse in the outdoor shower and a waterfront sunset on the rooftop deck.brbr-- THE PROPERTY --brbrRooftop Deck | Canal-Side Views | Boat Launch Nearby | New Modern Appliances | Kayaks & Bikes ProvidedbrbrBedroom 1: Queen Bed | Bedroom 2: Twin Daybed w/ Twin Trundle | Bedroom 3: Twin Daybed w/ Twin Trundle | Living Room: Queen Sleeper Sofa, Twin Sleeper SofabrbrINDOOR FEATURES: Newly renovated in 2021, 4 Smart TVs, remote workspace, dining table, ceiling fans, tropical-themed decorbrOUTDOOR AMENITIES: Multi-level deck w/ seating, tropical hut, waterfront seating & dining, gas grill (propane provided), private swim spa (no heat), cornhole set, swing chair, outdoor shower, boat dock (up to 24' boats, bring your own ties & bumpers), 3 adult-size kayaks, 1 child-size kayak, 3 adult-size bikesbrKITCHEN: Cooking basics, 4-burner range, microwave, dishwasher, spices, dishware & flatware, toaster, tea kettle, drip/Keurig coffee maker, blenderbrGENERAL: Free WiFi, washer/dryer, towels/linens, complimentary toiletries, hair dryer, iron/board, beach towels & chairs, central air conditioningbrFAQ: Access only by stairsbrPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrON-SITE FUN: Swimming, boating, fishing, kayaking, bike riding, wildlife viewingbrTHE BEST OF KEY WEST (~10-15 miles): Key West Lighthouse, The Hemingway Museum, Southernmost Point of the Continental USA, The Key West Butterfly & Nature Conservatory, Florida Keys Eco-Discovery Center, The Key West Amphitheater, Truman Little White House, Key West Shipwreck Museum, Mel Fisher Maritime Museum, Audubon House & Tropical Gardens, Fort Zachary Taylor State Historic ParkbrBEACH DAYS: Sugarloaf Beach (6 miles), Boca Chica Beach Park (7 miles), Smathers Beach (13 miles), Higgs Beach (15 miles), Fort Zachary Taylor Historic State Park Beach (16 miles)brAIRPORT: Key West International Airport (13 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatherings br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: The swim spa does not have heat
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Exceptional(22)

$469.49

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Private Vacation Home

THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!

Key West, Florida, United States

**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrCLASSIC KEY WEST....brWhen only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dream island vacation. Located in Old Town and just steps away from the Historic Seaport.  You are in walking distance to some of Key West's best restaurants and boating adventures.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrAMENITIES...brThis beautifully landscaped home with gracious sitting porch awaits you and your family. Newly renovated master king bedroom and bath are located on the main floor as well as a queen guest room with bath. A spacious great room that flows to the porches, pool and great outdoor space allows for family gatherings and hours of entertaining.  Updated kitchen looks over Sawyer Lane and opens to the pool area for easy outdoor dining.  Lovely Dade County Pine floors throughout and plenty of natural Key West sunshine from the many windows and doors. The second floor has a bonus room featuring a king, bath, office and rooftop sun deck. brbrPARKING...brThere is parking for up to two vehicles in gated driveway.brbrPETS...brThis home is not pet-friendly, however the owner may consider making exceptions for certain sizes/breeds. Please feel free to inquire in advance of booking.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)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). brbrLIVE THE CHARMED LIFE...
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Exceptional(27)

$451.94

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Condo

Sky Loft - Steps from Duval Street & Shared Pool

Key West, Florida, United States

Summary:brbrExperience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duval Street, this top-floor gem puts you right at the heart of the action. From vibrant bars and restaurants to must-see local attractions, adventure is just steps away.brbrbrbrUnwind by the inviting pool, complete with cozy lounge chairs, and soak in the island vibes.brbrbrbrBright, airy, and perfectly located, Sky Loft offers incredible value for couples or friends looking to enjoy the ultimate Key West experience!brbrbrbrThe Space:brbrThis bright and airy 1-bedroom, 1-bathroom space features an open-concept living area, a private balcony, and all the comforts of home. The fully equipped kitchen has stainless steel appliances, including a refrigerator, microwave, and stove. With AC, free WiFi, a private washer and dryer, and access to a shared pool, Sky Loft has everything you need for a relaxing stay.brbrbrbrBed and Bathroom Layout:brbrbrbr1 King-size bedbrbr1 Queen sleeper sofabrbrPerfect for couples or small groups, Sky Loft offers comfort, convenience, and a touch of island charm.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code 3 days prior to check-in to enter the unit.brbrbrbrShared community features: shared pool, lounge chairs and seating areabrbrbrbrHow to access: This unit is accessed by 2 flights of stairsbrbrbrbrThe Neighborhood:brbrThis unit is located on the highly touted Southard Street, just steps away from the world-famous Duval St, the Historic Seaport, and a variety of restaurants, coffee shops, and bars.brbrbrbrGetting Around:brbrParking Information: Unfortunately, there is no on-site parking for this unit. brbrbrbrFor overnight parking, here are some parking lot options:brbr• Fleming Street Pay-to-Park Lot (This is Closest to you!)brbr• 204 Simonton Streetbrbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrbrbrStreet parking information:brbr• There are pay-to-park spots and meters - it is free from 12am - 8pm. There is a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbr​​- One block from Duvalbrbr- Private washer/dryer in unitbrbr- This unit is on the 3rd floor of the complex and is not recommended for guests with mobility issuesbrbr- This unit is about 10 minutes from the airportbrbr- This unit is not pet friendly
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Bath 1

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Sleep 4

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$326.17

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Condo

Oceanfront living in Key West by Rent Key West Vacations

Key West, Florida, United States

Life is best lived from the balcony of this tranquil oceanfront condo. Feel like your feet are touching the sand, but yet your balcony is a floor above the actual sand with both sunrise and White St Pier views. This is a new unit to the rental program and therefore doesn't have reviews yet! Don't let that stop you from renting!brbrThis oceanfront oasis is located in the Key West Beach Club, an upscale, gated community with two oceanfront pools, pavilion area, workout room and tennis court. The Key West Beach Club is one of the very few condo communities on the island that sits directly on the coastline.brbrEnter the open living, dining, kitchen with your eye drawn immediately to the view. The living room has light blue walls with dark wood flooors and features a modern sectional leather sofa with leather accent chairs & natural wood accent tables. The dining area has a spacious natural wood Room and Board dining table for 6. The kitchen features a full wall of cabinets and stainless appliances The coffee bar is a nice feature to enhance the kitchen. It is the counter height table in the kitchen that steals the show, with its surfboard inspired design and bar stools as another dining space or perfectly used as a serving area.brbrThe Primary Bedroom has been updated with a king tropical style bed and new mattress. The ensuite bath has a long vanity and large walk in shower. A concealed window in the shower allows you to see the ocean while showering, but the view is obscured from the bedroom for privacy. The guest room features a queen bed and desk for multi-purpose use of the space. A hallway door between the guest room and guest bath will close to allow the large bathroom with walk-in shower to serve as a second ensuite.brbrThe balcony offers a lounge area, outdoor dining and chaise lounge chairs for relaxing oceanside. brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, garage parking and elevator access.brbrCommunity Amenities: Resort-type amenities include two oceanside pools (heated), tennis court, outside cooking facilities and pavilion, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the right when exiting the property and Higgs Beach is just past White Street Pier to the left. There are plenty chaise lounges around the pool areas as well as the covered pavilion to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the late spring and summer. This is a natural phenomenon that is outside of our control.brbrPlease note: This is a Monthly vacation rental with a minimum stay of 29 days, excluding February.
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Bath 1

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Sleep 4

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