Vacation Home Rentals By Owner In Key West, FL

Discover this 3-bedroom gem in Key West. This tranquil townhome offers a wonderful escape for guests. With 1 king bed and 2 queen beds, everyone will feel welcomed in this cozy space. Enjoy the convenience of AC, WiFi, and a washing machine during your stay. Relax in the fitness room or unwind in one of the 3 bathrooms equipped with a shower and bathtub. Enjoy your time in Key West at our townhome. 2 parking spaces under the house

Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$331.68

Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf Course.brbrThis unique corner unit offers a generous, newly remodeled floor plan furnished to perfection. Enjoy privacy and luxury with a large fenced yard and your very own private pool featuring a serene waterfall, all overlooking the picturesque 2nd fairway.brbrTurnkey rental — perfect for guests to enjoy the season as if it were their own. Tastefully decorated and thoughtfully stocked, this home truly has it all.brbrHome Highlights:brbrCorner unit with fenced front and back yardsbrbrPrivate pool with waterfall featurebrbrOutdoor covered and screened lanaibrbrSpacious backyard with brick pavers and lush landscapingbrbrBreathtaking golf course views from backyard and master suitebrbrFirst Floor:brbrComfortable living room with sofa, chair, console, and 55” smart flat-screen TVbrbrDining room with seating for 4brbrUpdated kitchen featuring stainless steel appliances (stove, microwave, dishwasher, refrigerator) and breakfast bar with seatingbrbrPowder room for guestsbrbrBright family room with large sliding doors overlooking the fairwaybrbrUpstairs:brbrBedroom 1: Two twin beds, ample natural light, ceiling fanbrbrBedroom 2: Queen bed, large windows, ceiling fanbrbrBedroom 3 (Primary Suite): King bed, panoramic golf course views, ceiling fan, ensuite bathroom with vanity and shower, plus an in-suite laundry closet with stackable washer/dryerbrbrFull bathroom with vanity and showerbrbrCommunity Amenities:brbrSecure gated community with scenic meadowed paths ideal for walking, running, or playingbrbrAccess to two community pools (one heated)brbrWorkout room and play areabrbrParking for two vehiclesbrbrLocation Perks:brbrLocated at MM 2 off US 1, just one block from Key West Hospital, Police Department, Community College, and Tennessee Williams TheaterbrbrOnly 5 miles from downtown Key Westbrbr1.8 miles from Stock Island MarinabrbrThis home also includes a mid-stay cleaning service scheduled halfway through your rental period.brbrPlease note: This is a pet- and smoke-free property.

Fairway Villa w/ Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$215.89

Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Historic District, but built in 2000 and totally remodeled in 2017. Walking distance to many of the Old Town Key West attractions. Main house is two stories with 1 bedroom, 1 bathroom, kitchen and a living room and features 2 flat screen HDTV's with premium cable. Fast, reliable internet is also included for those of you that need to do some work while staying in paradise. Upstairs bedroom has high ceilings and double doors leading out to your own private balcony with views of the pool, courtyard & cottage below. Kitchen / Living Room have double doors that open to the courtyard and pool and also a single door to the covered patio, outdoor dining area and cottage. There is a sleeper sofa in the living room with a memory foam mattress. The cottage affords you another bedroom with a wet bar, another bath & high ceilings. Queen sized plush mattress is in the Murphy Bed that when up, can function as an additional family room and when down the bedroom. The cottage features brand new full sized Samsung washer and dryer and also has its own brand new central a/c. This home also has a new top of the line kitchen with wood cabinets, full sized stainless steel appliances, marble counters, and plenty of storage. Both bathrooms are updated with glass inlays, porcelain tile and new vanities. The brick driveway (off street parking) provides plenty of room for parking your car, golf cart and kayak. There is even an additional spot in front of the house. Come see the designer coastal touches throughout. Location, spacious fenced yard, off street parking, detached cottage for your guests, private pool, this is island living at its best! All windows and doors are impact (the home is very quiet). The pool and patio were recently renovated to add additional luxury and comfort for your stay. The outdoor overhang has 3 fans to give you that nice island breeze!

Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!

Key West, Florida, United States

Bed

Bath

Sleeps

$356.1

BAHAMA VILLAGE TREASURE...brDelight in being tucked away in your serenely quiet haven that is also just around the corner from all the excitement of our southernmost island. This Key West charmer is just a short stroll away from the Lighthouse, Hemingway House, award-winning restaurants, delightful shopping, beaches, and all the unique excitement of Duval Street. Once you arrive and park your car, your bike or flip flops will take you everywhere you'll want to go!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrAMENITIES...brThis quaint retreat greets you with a relaxing front porch that beckons you to sit and stay a while. Enter into a light and airy space where you immediately discover a modern and abundantly-stocked galley-style kitchen that has everything a foodie could desire for turning out your favorite family feasts. State-of-the-art appliances and kitchenware will inspire culinary creations for days. Carry your crafted cocktail into the living and dining areas where you can sink into a cozy couch or cushioned chairs for a fun book escape or binge watch your favorite show on the wall-mounted television. A dining table for 6 looks out onto the backyard area with moving glass walls and door. This property is equipped with a security camera on the driveway of the home.brbrSLEEPING ARRANGEMENTS...brThe king primary suite downstairs boasts profuse Florida sunshine coming from multiple windows. Sip your morning coffee from the plush window chair and plan your island adventures. A hanging closet, dresser and bed storage offer ample space for your vacation wardrobe. The downstairs bathroom consists of a large glass and tile shower, single granite sink, as well as a standard size stacked washing machine and dryer. Travel up the stairs to two more bedrooms. The queen bedroom has a closet and dresser for clothing storage, and a small television. It shares a jack and jill bathroom - with glass and tile shower and single sink - with the other bedroom that is furnished with two twin beds (can be converted to a king). The twin bedroom offers a flat screen TV as well. This last bedroom offers an oversized closet for clothing and storage. A sleeper sofa resides in the living room for additional sleeping arrangements. brbrOUTDOOR LIVING...brFrom the living and dining area, open the retractable glass sliders to bring the lush landscaped outdoor space inside. Sultry breezes invite you to step into your private black bottom dip pool (comes heated in the cooler months, or you may request to have it chilled in the summer months) while your dinner is sizzling on the outdoor grill. Enjoy stargazing from the comfortable outdoor furnishings with views of the lighthouse and plan your next amazing day in paradise! brbrBIKES...br5 bikes are included so you can ride through the beauty of the island at your leisure. brbrPARKING...brOff street parking for a smaller vehicle is included which makes coming and going a breeze!brbrPETS...br2 pets are considered at this property and a pet fee is required. Please include the size and breed in the 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 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).brbrSTEP INTO THE FUN....

KEY LIME COTTAGE ~ Stunning 3 BR/2Ba with Pool & Incredible Location!

Key West, Florida, United States

Bed

Bath

Sleeps

$431.28

Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, the main 2/2 house features an indoor/outdoor ethos that is reflected throughout. The bright cathedral ceiling living room spills out onto the covered and screened in patio, the master bathroom French doors open to the large swimming pool, and the master bath invites you to take a plunge in the outdoor heated spa.brbrThe separate 1/1 guest cottage is almost too cute for its own good – your guests will not want to leave! Bright, cool, and unassuming, this small space has all its own charm.brbrTHE LOCATIONbrThe house is located on one of THE most desired locations in Key West – on the end of one of the most beautiful and quiet lanes in center of the old historic district and arguably one of the most pleasant neighborhoods. “In the middle of it all, yet worlds away,” would be a great description. The Historic waterfront is a short four blocks away, as is bustling Duval street. Less than two blocks away you’ll find the best Cuban coffee at 5 Brothers, Help Yourself organic restaurant and produce market, homemade pasta at Mangia Mangia, and the famous Michaels restaurant. This is the Key West living everyone is looking for.brbrTHE LIVING AREAbrThe living room and dining area opens up to a covered and screened in porch, allowing you to enjoy your meals and relaxation inside or out. Two comfy couches in the living room invite you to curl up with a good book, with plenty of natural light from the large windows and multiple French doors.brbrTHE POOL AREAbrThis is where you’ll end up spending a lot of your days. Composed of both sunny and shaded areas, the pool area features a large pool, a separate hot tub with air jets, expandable teak table with 6 matching chairs, and 3 Barlow Tyrie teak chaise lounges with pull out drink trays. There is also a gas fired BBQ grill for afternoon cookouts.brbrTHE GARDENbr In tightly packed Key West, gardens can be a luxury, and this 6,425 sq. ft. property has the room to spread out. The tropical garden is framed overhead by a spectacular Royal Poinciana tree and surrounded by my majestic palms. The understory plants have been carefully chosen to provide year-round flowers, from colorful hibiscus, native and exotic flowering trees and butterfly attracting plants, to the wild orchids growing throughout the property. There’s always something blooming at Casa Escondida!brbrTHE ACCOMMODATIONSbrThere are two bedrooms and two bathrooms in the main house, plus the detached guest cottage and bathroom. All of the bedrooms have flatscreen TVs and cable/DVD players. The master bedroom has double French doors that open to the pool via a private screened porch and features cathedral ceilings and a king sized bed. The second bedroom has double French doors that open to the private front porch and has a queen bed. The cottage has a queen bed and private bathroom, as well as two small private decks with outdoor chairs.brbrTHE AMENITIESbrbr• Central Airbr• Ceiling fansbr• Pool and outdoor hot tub with therapeutic air jets.br• Off-street gated parking for two carsbr• Lush, mature landscaping and wild orchids throughout propertybr• Outdoor furniture and chaise loungersbr• Outdoor showerbr• Full size washer/dryerbr• Gas BBQ grillbr• Cable, DVD players and flat screen TVsbr• Wireless High-speed internetbr• Bose Bluetooth wireless speakers

Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6

Key West, Florida, United States

Bed

Bath

Sleeps

$2029.65

The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedrooms and seven bathrooms. The house interior recently received a new coat of paint, new furnishings and some additional redecorating projects were completed.brbrThe Mansion and its beautiful pool and outdoor living space is ideal for large family gatherings or intimate corporate getaways. This private, secure vacation property is steps away from famous Duval Street, the historic seaport and everything that old town Key West has to offer.brbrUpon entering you will notice the beautiful, 12’ high original ceilings. There is a traditional front parlor living room, a family room, dining room, and a kitchen featuring granite counter tops and stainless-steel appliances. There are also two bedrooms and two full bathrooms on the first floor. brbrThe first bedroom has a new queen size bed. The bedroom bathroom is ensuite. This bathroom has a tub/ shower combination with a dramatic high tiled archway above. The original solarium is now home to a unique bedroom with Cuban tile floors and an ample king size bed. The bathroom is across from this bedroom and has a tiled walk-in shower.brbrThe banister from the 1890’s and the beautiful chandelier will guide you up the staircase to the four bedrooms and four bathrooms that are on the second floor. brThe front bedroom has a queen size bed and French doors leading to the balcony that spans the entire width of the house. This balcony offers a wonderful view of the historic neighborhood’s streetscape below. The ensuite bathroom is finished in tile and has a walk-in shower.brbrThe west bedroom offers a king size bed. The room has knotty pine wainscoting, original Dade County Pine wood planked floors, and large sash windows. The bathroom is also ensuite with a tile walk-in shower.brbrThe east bedroom contains a king size bed and features island style wicker furnishings. The ensuite bathroom has a tiled walk-in shower.brbrThe back bedroom has a modern aesthetic with a king size bed and two sets of French doors leading to the back balcony overlooking the outdoor living space and swimming pool. The ensuite bathroom has double sinks and a tiled walk-in shower.brbrThe third floor offers a unique, private, split-level suite with its own media area, wet bar with expansive countertops, king size bed nook, an additional sleeping space, and a full bathroom. The suite has beautiful hardwood floors and offers an inviting private balcony with a view of the pool area. The bathroom’s two skylights are a unique feature bringing in the natural light.brbrA bonus privacy and safety feature of this house is an exterior back staircase to the second and third floors. The exterior also offers outdoor living at its tropical finest. brbrGuests will enjoy the spacious sun deck and the large swimming pool. The Mansion’s outdoor space is perfect for lounging, grilling and poolside dining and entertaining. The large swimming pool may be heated in the cooler months and delightfully refreshing during the rest of the year.brbrThe Mansion Bedding Summary:br• 1st Floor - 1 King, 1 Queen size bed br• 2nd Floor- 4 Kingbr• 3rd Floor – 1 KingbrbrThe Mansion Parking:brTwo off-street parking spacesbrbrAlthough completely separate and private, the Mansion is on the Watson House Grand Estate. Should you need additional accommodations for a larger group or if you just wish to spread out, the gate in the southeast rear corner of the pool area can be unlocked and opened to the Villa at the Watson House Estate adding another pool area, four bedrooms and bathrooms for your enjoyment. Click on The Watson House Grand Estate for details.

CLASSIC KEY WEST - Grand home in Old Town location

Key West, Florida, United States

Bed

Bath

Sleeps

$3092.17

The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gatherings or intimate corporate getaways. It is steps away from Duval ST, the seaport and everything old town has to offer.brbrThe 1840's Mansion is a lovingly restored and renovated 3 story Victorian home with 7 bedrooms and bathrooms. Interior painting and some additional redecorating projects were recently completed and new furnishing were added. brbrUpon entering, notice the beautiful, 12’ high original ceilings. There is a front living room, a family game room, dining room, and a kitchen featuring granite counter tops and stainless-steel appliances. There are also 2 bedrooms and baths on the first floor. brbrThe New Orleans themed bedroom has a four poster queen bed. The bathroom is ensuite and has a tub/ shower combo with a dramatic high tiled archway above. The original solarium is home to a unique bedroom with Cuban tile floors and an ample king bed. The bathroom is nearby and has a tiled walk-in shower. brbrThe banister from the 1890’s and beautiful chandelier guide you up the staircase to the 4 bedrooms and 4 bathrooms on the 2nd floor. The front bedroom has a queen bed and French doors leading to the balcony that spans the width of the house and offers a view of the historic streetscape below. The ensuite bathroom is finished in tile and has a walk-in shower. The west bedroom offers a pencil-style four poster queen bed. The room has original Dade County Pine wood planked floors and large windows. The bathroom is ensuite with a tiled walk-in shower. The east bedroom contains a king bed and features island style wicker furnishings. The ensuite bathroom has a tiled walk-in shower. The back bedroom has a modern aesthetic with a king bed and two sets of French doors leading to the balcony overlooking the outdoor living space and pool. The ensuite bathroom has double sinks and a tiled walk-in shower.brbrThe third floor offers a unique, private, split-level suite with its own media area, small kitchen, bedroom with a king bed, and a full bathroom. The suite has beautiful hardwood floors and offers a private balcony with a view of the pool area. The bathroom’s two skylights are a unique feature bringing in the natural light and one is actually above the walk-in tiled shower. A bonus privacy and safety feature of this house is an exterior back staircase to the second and third floors. brbrBetween the Mansion and the Villa lies a large sun deck and the first of 2 pools. This area is perfect for lounging, grilling and poolside dining. The pool may be heated in the cooler months and delightfully refreshing during the rest of the year.brbrThe Villa is located at the rear corner of the pool area. Those staying here may also park and enter and exit through the villa's front entrance. The Villa’s soothing color palate welcomes you with warm sand tones and relaxing hues of blue. The design is a balance of modern furnishings with some leather and wood. The beautiful travertine marble floors are laid throughout the house. The open concept living, dining and cooking offers a kitchen with sleek wooden cabinets, granite counter tops, top-of-the-line appliances and fixtures. brbrAll of the bedrooms are ensuite; 3 have king beds and 1 has 2 twins which can be made into a king. The bathrooms in the king rooms have walk-in, tiled showers and the bedroom with the twins offers a bathtub with in-tub tiled shower.br brThe L shaped pool with jacuzzi jets curves around to a covered deck with a long granite bar-top with seating which also provides the perfect place for arranging a poolside buffet.brbrMansion Beddingbr1st Floor - 1 King, 1 Queen br2nd Floor- 2 King, 2 Queen br3rd Floor – 1 KingbrbrVilla Beddingbr2 King, 1 CA King, 2 Twin beds (which can be made into a King)brbrParking: Three off-street parking spaces; 2 at the mansion and 1 at the villa. brbrThere may be times when scheduling allows for the rental of the Mansion or the Villa individually. The gate between the properties is closed and locked making each home separate and private.

WATSON HOUSE GRAND ESTATE on Simonton St

Key West, Florida, United States

Bed

Bath

Sleeps

$1128.84

The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everything that old town Key West has to offer, but its privacy fencing and quieter location offer a secure, relaxing retreat.brbrThe Villa’s soothing color palate welcomes you with warm sand tones and relaxing hues of blue. The design is the perfect balance of modern furnishings, some leather and wood. The beautiful earth tone travertine marble floors are laid throughout the house. The open concept living, dining and cooking offers a kitchen with sleek wooden cabinets, granite counter tops, top-of-the-line appliances and fixtures. brbrAll of the bedrooms are ensuite; three of the bedrooms have king size beds and one that has two twins, which can easily be made into a fourth king. The bathrooms in the king size bedrooms have large walk-in, tiled showers and the bedroom with the twin beds offers a bathtub with in-tub tiled shower. brStep through the living area sliding glass door and onto the deck where your inviting custom designed L shape pool with jacuzzi jets awaits. The decking and pool curve around the villa where you will find a covered deck with a long granite bar-top with seating which also provides the perfect place for arranging a poolside buffet brunch, lunch or dinner. French doors lead back into the open concept living space.brbrThe Villa Bedding Summary:br3 King, 2 Twin size bedsbrbrParking: brOne off-street parking space brbrAlthough completely separate and private, the Villa is on the Watson House Grand Estate. Should you need additional accommodations for a larger group or if you just wish to spread out, the gate in the northwest rear corner of the property can be unlocked and opened to the Mansion at the Watson House Grand Estate adding another outdoor living space, swimming pool and seven bedrooms and bathrooms for your enjoyment. Click on The Watson House Grand Estate for details.

PERFECTION...STEPS FROM DUVAL ~

Key West, Florida, United States

Bed

Bath

8

Sleeps

$509.36

Experience the vibrant charm of Key West with a stay at Sea Esta Suite, a stunning two-story townhouse located in the exclusive Duval Square condominium complex. Perfectly situated at the intersection of Truman Avenue and Duval Street, this vacation rental puts you just steps away from world-class dining, shopping, and iconic attractions like the Southernmost Point, all while offering private garage parking and rooftop pool access for a relaxing escape.brbrThe Ambiance:brSea Esta Suite is the ultimate retreat for up to six guests, combining modern comfort with tropical charm. The townhouse features a bright and airy living space with two king bedrooms, each with en suite bathrooms. The master suite includes a private balcony and walk-in closet, while the second bedroom offers comfort and convenience. Additional sleeping accommodations are available on the queen-size pullout couch in the spacious living area.brbrThe newly renovated kitchen comes fully equipped with modern appliances, perfect for preparing meals to enjoy on your private patio or balcony. Relax by the large shared pool, take advantage of free WiFi, or unwind in front of one of the suite's cable TVs after a day of exploring Key West.brbrGuest Perks:brGuests will enjoy seamless self-check-in with a personalized access code provided before arrival. Sea Esta Suite also includes a private garage parking spot, a private washer/dryer for convenience, and access to a rooftop pool for soaking up the Key West sunshine.brbrNeighborhood Highlights:brNestled on the 1000 block of Duval Street, Sea Esta Suite offers unbeatable access to Key West's best attractions. Stroll just 10 minutes to downtown Key West for lively bars, unique shops, and unforgettable restaurants. For dining closer to home, Duval Square boasts local favorites like New York Pasta Garden and Origami Sushi right below the complex.brbrTake a short walk to the Southernmost Point for a photo op or explore nearby art galleries and nightlife. The property's prime location ensures that all your Key West favorites are within easy reach, from historic landmarks to vibrant nightlife and everything in between.brbrTransportation Tips:brWith its central location, exploring Key West is easy and enjoyable. Many attractions are within walking distance, but you can also rent a bike, scooter, or golf cart to venture farther. Private garage parking is available for one vehicle, making it convenient for guests with cars. Need recommendations Just ask—we're here to help!brbrOther Things to Note:br- Private washer/dryer included in the unit.br- Shared heated pool on-site.br- This property is not pet-friendly.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrReserve your stay at Sea Esta Suite today and experience the best of Key West with the perfect mix of convenience, comfort, and tropical charm!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Sea Esta Suite | Located On Iconic Duval w/ Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$288.9

YOUR PEACEFUL PARADISE AWAITS…brFind this unmatched island escape tucked away in the lust and intimate Southernmost Cabana Community in the Old Town district of Key West. Convenient location with high end finishings and endless amenities, this home is sure to complete your well awaited tropical getaway in style! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brPull up to your tropical abode boasting vibrant vegetation all around immersing you into the island lifestyle. Step onto your own front porch with rocking chairs for your morning cup of coffee as you appreciate your serene surroundings. Inside you will be greeted by a cheery, open great room showcasing tile flooring and natural lighting all around. Prepare your meals together in a fully equipped kitchen complete with granite counters and stainless-steel appliances with bar seating for 3 and a nearby dining table for 4. Snuggle up on cozy living room furnishings with a flat screen TV available and stunning garden views beyond a set of French doors to your outdoor Paradise.brbrSLEEPING ARRANGEMENTS...brFollow the stairs up to a king bedroom with a flat screen TV and an en suite bathroom with a shower. Down the hall you will find another guest room equipped with a queen bed, flat screen TV, an en suite bathroom with a shower and your own private balcony. An additional full bathroom with a shower lies off the kitchen area downstairs. brbrOUTDOOR LIVING...brYour own slice of paradise is available as you step out onto your own back porch with an inviting seating area and grill for your fresh catch of the day. Take a stroll through the quaint community and find your tranquil heated community pool with a waterfall and surrounding loungers. Take a short bike ride or walk down to the unique treasures of Duval Street or sneak away to a nearby beach. The home also comes with a parking spot right out front of the unit. brbrPETS...brNo pets please.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…

INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$172.82

Tucked away in a quiet Old Town Key West neighborhood you'll find Nauti's Nest, a cozy and comfortable two bedroom cottage with all of the comforts of home. brbrThis carefully curated space features two charming queen bedrooms, an open-layout kitchen and living area, peaceful front porch, tranquil swimming pool, and essential amenities like AC, washer/dryer, and fast WiFi. The home offers convenient off-street parking - a true luxury in Key West! brbrThis cottage's ideal location is within a short stroll to Key West's beaches and lively Duval Street where music, nightlife, and world-class dining await.brbrSoak up afternoon rays by the pool, cool off in the cold central AC, or open the windows and let those famous tropical breezes drift through. Sip cocktails with friends on the front porch or poolside. Prepare breakfast in the well-equipped kitchen before heading out to explore the island. Nauti's Nest is your ideal home-base in Key West.brbrDogs are welcome guests if registered and approved in advance. The maximum size is 30 lbs. They must be crated when left alone in the home and not barking or disturbing neighbors. The guest must clean up all pet messes inside and outside of the home. Damages or extra dirtiness will result in additional fees. Please place a tray under your pet’s water and food bowls to prevent moisture damage to the wood floors. Please ensure the dog is groomed with nails trimmed and filed prior to arrival to prevent scratches.

Charming 2 Bedroom Cottage in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$282.38

Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!! brbrThe Hollinsed House's 1st Floor - ShangriLa Suite is a large deluxe studio with a queen bed, living area, bath and kitchen that is tucked away for privacy with its own private courtyard. Sleeps 2brbrHave a group coming to Key West Or maybe need just one or two more units Go to Click Here to see All My Rental Listings just above the Map Feature to see the rest of my listings at the Hollinsed House!brbrRATES for SPECIAL EVENTS:brPlease note that rates for Fantasy Fest, Meeting of the Minds (formerly Jimmy Buffet Parrothead Days), Race Week, Thanksgiving, Christmas, New Years, Songwriter's Festival, Memorial Day Weekend, Hemingway Days, and Poker Run all have minimum stays and different rates than are listed on the Rates page of this VRBO listing. brbrbrDEPOSITS:brA deposit equal to the cost of one half of your stay or one night, whichever is greater, is required to guarantee a reservation. The balance is due 30 days prior to arrival. Sorry, no refunds for early departures.brbrCANCELLATION AND REFUNDS:brCancellations from time of booking to thirty (30) days of arrival date will be charged a $50.00 processing fee per unit rented. All bookings of one week or longer will be charged a $100.00 processing fee per unit rented if cancelled more than thirty (30) days prior to arrival. Cancellations within thirty (30) days of arrival date will be charged for one night per unit rented or may extend their reservation for six months. Cancellations within seventy-two (72) hours to twenty-four (24) hours have a 50% cancellation fee or can be extended for six months. Cancellations within twenty-four (24) hours are non-refundable but will be offered a six-month extension. Sorry, no refunds for shortened stays. We reserve the right, to change your unit number if you are reserving for 3 nights or less.brbrCancellations for Special Events: Fantasy Fest and Christmas/New Years. Reservations of 5 days or longer that are cancelled within 2 weeks of arrival will be charged a $250 cancellation fee. Reservations cancelled within 1 week of arrival will be charged a $500 cancellation fee. Reservations cancelled within 72 hours of arrival are non-refundable. All cancelled reservations will be offered a six-month extension. brbrHURRICANE SEASON CANCELLATION POLICY, EFFECTIVE JUNE 1 -DECEMBER 15TH:brWe do not refund for inclement weather or other circumstances beyond our control. We strongly encourage the purchase of Travel Insurance to protect your vacation investment! In the unlikely event that a hurricane evacuation is ordered while you are a guest, and you have not purchased travel insurance, you will be issued a voucher for the unused portion of your stay. Guests holding a confirmed reservation who are unable to travel to The Hollinsed House because of the closing of the Key West Airport or connecting roadways due to a mandatory evacuation and have not purchased travel insurance will receive a voucher in the amount of the room deposit held. Vouchers are redeemable between June 1 and December 15, up to one year from the issue date, excluding special events and holidays. (Exception: Vouchers issued for cancellations of Fantasy Fest reservations can be applied to future Fantasy Fests in the ensuing two years.) No voucher will be issued if the hurricane is not a threat to Key West and you are unable to travel because of canceled flights or adverse travel conditions outside the Keys. We strongly encourage the purchase of Travel Insurance to protect your vacation investment!brbrKeywords: Guest House, Condo, B&B

ShangriLa Suite / Queen Studio / Sleeps 2

Key West, Florida, United States

Bed

Bath

Sleeps

$167.75

Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located directly off of the elegant, resort style pool and you are just steps away from relaxation! We offer a two-story townhome with kitchen, dining area, powder bathroom and living area downstairs that opens to a large, screened in patio. Upstairs offers two bedrooms with a main, full bathroom. The primary bedroom has a king bed with an adjoining screened in patio that looks directly to the lush, tropical setting of the pool. The second bedroom offers a king bed with available desk space to work from paradise. The home does offer a full size washer and dryer for use during your stay. You are just a short jaunt to the clubhouse where you can play a nice round of golf at the Southernmost Golf course. All the necessities are available to you, all you need is your swimsuit and a pair of flip flops! Pack you bags and head to Poolside Paradise!

Poolside Paradise in Key West Golf Club

Key West, Florida, United States

2

Bed

1

Bath

Sleeps

$413.44

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrAfter landing in Key West and arriving at your door, FLIGHT OF THE FLAMINGO will have you feeling like it was love at first flight! The light colors, natural wood finishes, and Caribbean-inspired art radiate an energy and warmth reflecting Key West’s tropical vibes. From the rocking chairs on the veranda to the inviting interior and the lushly landscaped oasis in the backyard, FLIGHT OF THE FLAMINGO will have you relaxing in no time. Paired with Last Key Realty’s renowned Five-Star Guest Services and Concierge Team, FLIGHT OF THE FLAMINGO is the perfect place to perch yourself for a month (or longer!) in Key West.brbrTHE LIVING AREA…brbrThe spacious living area is situated at the rear of the home, featuring a large flat-screen TV surrounded by comfortable seating options for everyone in your group. The wall-to-wall glass sliding doors allow a ton of natural light to flow in. Preparing gourmet meals from home is easy thanks to the fully equipped kitchen with top-of-the-line appliances. The indoor custom-made dining table sits right next to the kitchen and offers seating for five with four more seats at the kitchen island. In the hall, you will find the powder room, which was beautifully hand-painted by local artist Katlin Spain!brbrTHE POOL AREA...brbrA truly distinctive feature of this home is the large sliding doors on the back of the house that create an unrivaled indoor/outdoor living space. Step out to the fully fenced backyard, surrounded by tropical landscaping that provides maximum privacy. brbrTake a dip in the pool, which can be heated in the cool months or cooled in the warm months, to relax after a long day of exploring the streets of Old Town. The backyard gets plenty of sun, allowing you to take full advantage of the chaise lounges on the pool deck for soaking up some rays. The unique mural enhances the colors and vibrance of this backyard oasis.brbrTHE ACCOMMODATIONS...brbr** Primary Bedroom: Features a king bed, a flat screen TV, a closet, and en-suite bathroom with a walk-in shower.brbr** Second Bedroom: Features a queen-size bed, a flat screen TV, a closet and shares a Jack & Jill bathroom with Third Bedroom.brbr** Third Bedroom: Features a full bed, a flat screen TV, and shares a Jack & Jill bathroom with Second Bedroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Smart TV in Living Roombr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Outdoor Showerbr** Propane BBQ Grillbr** Pool ChillerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 5 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.

Key West, Florida, United States

Bed

Bath

Sleeps

$1262.64

THE PROPERTY: Awarded the Florida Keys Preservation Star, this stunning home and outdoor space will entice you to live like a local. From its covered front porch to its rear entertaining area, you won’t want to leave. As you enter via the sunny yellow doors you will be captivated by the gingerbread balustrade, staircase book nook and beautiful Dade County pine walls. brbrMoving into the open concept kitchen and living room, high ceilings, designer finishes and natural light will greet you. The sleek white kitchen is equipped with stainless steel appliances and everything you need to prepare meals or snacks. The oversized island has seating for six and allows you to mingle with guests in the comfortably furnished living room. You will be drawn to the outdoors via the double set of sliders that spill onto the lanai. Unlike other lanais this one is generously furnished and includes a large screen TV and an air conditioned half bath. From here you can take a dip in the pool, sip cocktails or simply relax with a good book. The pool includes a water feature, and the entire area enjoys privacy via fencing and lush landscaping. Nap on a lounger while surrounded by palm trees and sunshine. A wonderful island option is alfresco dining. The chef in your group will enjoy the gas grill and large dining table. brbrAll three bedrooms in this home have ceiling fans and en suite baths with walk in showers. Two king bedrooms are located on the first floor, and one has direct access to the pool. You will appreciate the beautiful linens, natural light, and closet space. The third bedroom is located on the second floor. It has a queen bed and provides a bit of privacy for those who may need it. This room also has a vaulted ceiling, closet, TV, and plenty of natural light. brbrThis lovingly restored home has unique island charm and is in a fabulous location. If modern amenities, outdoor living, and walk-ability are on your Key West bucket list, Lilly's Pad is the vacation home for you!br brBED CONFIGURATION: There is a king en suite bedroom on the first floor. The second king en suite bedroom is also on the first floor. The third queen en suite bedroom is located on the second floor. brbrOUTDOOR AMENITIES: The covered lanai provides an outdoor living space with TV and plenty of seating. The dip pool with water feature is delightful after a day exploring the island. Dine alfresco on your large outdoor dining table. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A grill is available for cooking up the catch of the day. A convenient and air conditioned half bath is located off the lanai. Sunshine, palm trees and lounge chairs on the sun deck await you. brbrPARKING: There is a convenient off-street parking space with this home, which is a rarity in Key West.brbrLOCATION: Old Town just a half block from Duval Street. Near the Key West Butterfly Museum and Southernmost Point. You will enjoy this quieter yet walkable side of town near finer shops, galleries, and restaurants. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals.***

~LILLY'S PAD~ Upscale elegance with a private pool and parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$286.89

Unwind in the Beautiful, Tropical Paradise of Key West, in the Renowned 'Southern Comforts' 4 Bedroom Ocean Front Villa, in the Peaceful and Serene Environment of Bay Point on Lower Saddle bunch Key. Only 15 Miles Away is the Exciting, Eccentric and Much Beloved City of Key West, with its Many Attractions.br br But Before You Explore This 'Southernmost Tip' of the Us, You Are Seduced by the Comfort and Beauty of Your Vacation Home.br br the Beautiful, Designer Inspired But Comfortable and Charming Southern Comforts Villa, with a Magnificent Open Floor Plan Opens to the Ocean Front Space and the Large in Ground Heated Pool, Via Three Sets of French Doors. the Property Has Four Lovely Bedrooms; the Master Bedroom Opening to the Ocean Front Via it's Own Set of French Doors. The Master Bedroom has a large Master Bathroom. There is an Additional Full Bath Comfortably Located Between Two of the Guest Bedrooms.br br the Kitchen Has Been Recently Remodeled, as is the Rest of the Property, to Include Designer Cabinetry and All New Stainless Steel Appliances, with a New Dishwasher and Built in Microwave. the Designer Inspired Tiling Throughout the Home, Reflects the Care and Thought and Effort the Owners Have Invested in the Extensive Remodeling Project of the Property.brbr and Now, Humming Along with the Jimmy Buffett Tunes on the Stereo; You Sit by the Beautiful, Large, in-Ground Heated Pool on the Ocean Front, Sipping Your Own Personal Recipe for the Definitive Pina Colada, as You Watch the Magical Sunset of the Florida Keys! the Pool Has a Patio Adjacent to it; Making it an Ideal Location for Pool Side Dining and Entertaining.brbr However, If the Lure of the Open Water is Too Powerful to Resist, You Stroll Down to the Ocean Front Tile Patio and Dock Via a Few Gently Sloping Gracefully Curving Sets of Stairs. There You Will Find, Not Only Another Level of Possible Space for Dining and Entertaining, But Also Our Much Featured 'Sunset Swing' Under a Gently Swaying Palm Tree.brbr Heading North, Toward the Lovely Keys of Summerland and Big Pine Key with it's World Renowned Diving and Snorkeling Sites and the Key Deer Reserve or South, Toward the City of Key West, You Will Find Numerous Charming Ocean Front Dining Possibilities and Some Wonderfully Eccentric Restaurants with Great Sea Food and a Delightful Cast of Characters Serving You!brbr Margaretville, Jimmy Buffett, Ernest Hemingway, Tropical Sunsets, Swaying Palms and the 'American Caribbean' What Could Be Better Than This!brbr brbrKeywords: House

Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount

Key West, Florida, United States

Bed

Bath

Sleeps

$219.76

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a modern kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in closet, a private bath with a large shower. Another bedroom also opens to the pool deck area and is furnished with a queen size bed. The third bedroom has two twin beds. A second bathroom serves the guest bedrooms. Two walls of the living room have sliding doors that open completely onto the pool area.brbrKeywords: single family home in residential neighborhood available for 4 week minimum rental period

Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!

Key West, Florida, United States

Bed

Bath

Sleeps

$1722.99

Welcome to Key West OasisbrbrLuxury | Privacy | Iconic Location in Truman AnnexbrbrTucked away on one of the most exclusive lanes in the Truman Annex, Key West Oasis is a sophisticated, meticulously maintained estate that offers an unparalleled island escape. With 5 bedrooms, 5.5 bathrooms, and over 2,796 sq. ft. of beautifully designed living space, this estate is the ideal sanctuary for discerning travelers seeking comfort, style, and an unbeatable location.brbrPROPERTY HIGHLIGHTS:brbrTotal of 5 bedrooms / 5.5 bathroomsbrbr4-bedroom main house + 1-bedroom guest cottagebrbrLagoon-style heated saltwater pool & spabrbrRooftop observation deck with panoramic 360° Key West viewsbrbrLocated steps from Truman Waterfront Park, Duval Street & the beachbrbr4 cruiser bikes includedbrbrGated carport & lush tropical landscapingbrbrMaximum 8 guests | No pets | No eventsbrbrMAIN HOUSE (4 Bed / 4.5 Bath)brbrMain Floor:brStep into elegance with gleaming mahogany wood floors, a formal dining room with seating for 8, and an adjacent study complete with a built-in workstation. The open-concept kitchen connects seamlessly to the living area and features black granite countertops, stainless steel appliances, breakfast bar for 4, and fully stocked cooking essentials.brThe living room is centered around a 75” smart TV with sound system and opens directly to the stunning outdoor patio and pool area.brbrSecond Floor:brTwo guest bedrooms share a balcony overlooking charming Noah Lane—one with a queen bed, the other a full—plus a shared full bath. The spacious primary suite features a king-size bed, 55” smart TV, large walk-in closet, and a spa-like en-suite bath with soaking tub, dual vanities, and walk-in shower. French doors open to an expansive Ipe balcony—perfect for sunset cocktails.brbrThird Floor + Rooftop:brThe third floor features a cozy 4th bedroom with a full bed and an adjacent full bathroom. A second flexible room serves as an office, yoga studio, or meditation space, and includes a wet bar. French doors lead to a ship ladder ascending to the rooftop observation deck, offering 360-degree views of Key West and the surrounding turquoise waters.brbrGUEST COTTAGE (1 Bed / 1 Bath)brbrDetached for maximum privacy, the 239 sq. ft. guest cottage includes a queen bed, 55” smart TV, full bathroom, mini kitchen, and closet—ideal for visiting friends or family.brbrOUTDOOR LIVINGbrbrLagoon-Style Saltwater Pool & Spa – Heated with tranquil water featurebrbrOutdoor Dining & Lounge Areas – With ceiling fans for warm afternoonsbrbrGas Grill – Perfect for al fresco BBQsbrbrOutdoor Shower – Ideal after beach or pool timebrbrTropical Landscaping & Lighting – Enhancing the charm and ambiance of this classic Conch-style estatebrbrCARPORT & TRANSPORTATIONbrbrGated carport with space for vehicle or golf cartbrbr4 cruiser bikes provided—ride to the beach or Duval Street in minutesbrbrLOCATION, LOCATION, LOCATIONbrbrSteps from Truman Waterfront Park and AmphitheaterbrbrWalk to Fort Zachary Taylor BeachbrbrMinutes from Duval Street, Mallory Square, and top-rated restaurants, bars, and galleriesbrbrGOOD TO KNOWbrbrStrict maximum of 8 registered guestsbrbrNo parties, events, or amplified noise allowedbrbrNo pets permittedbrbrSecurity cameras on exterior only (front, rear entry, and driveway)brbrProfessionally maintained and cleaned to the highest standardsbrbrExperience Key West at its finest. Whether you’re sipping cocktails on the rooftop deck, enjoying a morning swim, or biking to local favorites, Key West Oasis is the perfect blend of luxury, privacy, and island charm.

Key West Oasis - Truman Annex Estate

Key West, Florida, United States

Bed

Bath

Sleeps

$703.13

Welcome to SOUTHERNMOST SUNSHINE! brbrLocated in the heart of Old Town Key West just a few steps away from the Atlantic Ocean, Southernmost Point and 1 block to Duval Street. brbrIt doesn’t get any better than this 4 bedroom / 3 bathroom 1938 fully restored historical home. brbrWhen you arrive the home you are greeted with picturesque curb appeal. A white picket fence surrounds the commanding two story French Colonial home. Large wrap around decks complete Carolina blue ceilings, dramatic navy blue plantation shutters, lush tropical landscape, mature canopy trees, the sound of birds whispering in the trees and the faint trickle of a fountain dripping into a small quaint pond below. You have finally arrived your own private paradise! brbrAs you enter the home through the front door the vaulted ceiling above and antique chandelier in the entry opens to a large living room which is full of natural light and has oversized windows, ceiling fan, plush sofa, sitting chairs and flows freely to the formal dining room at the rear of the home with comfortable seating for 8 guests. The room is complete with a set of french doors that open out to the back deck and outdoor dining area with gas grill. brbrFrom the dining room you enter a huge Chefs kitchen with a large center island, breakfast bar and is lined with preparation counter space that goes on and on. The kitchen is a Chef’s dream with every major kitchen appliance one could ever dream! A 6 burner gas range, two ovens, warming oven, built in refrigerator, dishwasher, a separate wet bar with ice machine, beverage refrigerator and an abundance of storage and space throughout. brbrOff of the kitchen is the mud room where the full-size washer & dryer are conveniently located and a butlers entry door to the driveway and front wrap around porch makes brining in groceries or beach equipment a breeze. brbrA hallway to the right of the main entry takes you to the downstairs full bathroom with shower and a spacious guest suite with lots of natural light, queen size bed, chest of drawers and sitting chair. brbrUpstairs you will find the primary suite at the rear of the home that offers a king size bed, chest of drawers, walk-in closet, sitting area/work station with desk, en suite full bathroom with shower and double vanity. A set of French doors open out to a private deck that allows a birds eye view of the pool area and spiral stairs leading down to pool deck. brbrTwo additional bedrooms and 1 full bathroom with shower/ tub combo are also located on the second floor. Bedroom 1 offers two twin beds and the other has a king bed. Both bedrooms have access doors to the upstairs balcony and sitting area.brbrThe fully manicured grounds are spread over 5, 000 sq ft and provide off-street parking for two cars. Mature palms are accented with landscape lighting to make the yard come to life after dark! The outdoor relaxation and entertainment areas are endless! The upper and lower large wrap around decks provide optimal views out to the Atlantic and Southernmost Point. A spacious rear deck surrounding the oversized pool also has a covered Pergola with ceiling fan and dining area. The last deck is accessible via a spiral staircase on the back pool deck or out the primary suite doors.brbrThe pool was refinished in 2022 and is complete with an outdoor shower, pool loungers, seating and is surrounded by a six foot privacy fence. brbrThis home has done a fantastic job of preserving the historical charm while adding in modern amenities and furnishings to ensure guests upmost comfort and enjoyment. It is sure to be a guest favorite and we look forward to hosting you at Southernmost Sunshine at the Southernmost Point of The Florida Keys! brbrbrbrbrbr

SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!

Key West, Florida, United States