Vacation Rentals By Owner In Key West, FL

$331.68

Fairway Villa w/ Private Pool

Key West, Florida, United States

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.

3

Bed

2

Bath

6

Sleeps

$675.0

/ Nightly

Apartment

Luxury Waterfront Stay @ The Galleon, Mins from Downtown

Key West, Florida, United States

Imagine waking up every morning in Paradise.brWith Balconies that overlook the marina and ocean. Private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the hot tub or sauna during your stay or work out in the on-site fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrThis spacious 2 bedroom condo sleeps 6, and features a fully equipped kitchen, including a full-sized refrigerator, microwave, toaster, coffee maker, stove and oven. The primary bedroom has a king sized bed, ensuite jacuzzi tub, as well as a full bathroom. The guest bedroom has 2 twin beds and a full guest bathroom. The living room has a tv with cable, dining area for 4 and a sleeper sofa. brbrGalleon Resort Marina serves breakfast. Guests can enjoy poolside drinks at Sunset Tiki Bar. 1 car permitted per unit onsite. brbrAdditional Fees due at hotel upon check-in:br $75.00 resort fee per week, along with a refundable $150 deposit, as long as no damages occur.

Bed

Bath

Sleeps

$1113.01

/ Nightly

House Boat

Luxury 2 stateroom Yacht FREE TIME

Key West, Florida, United States

Skip the hotel room-own the horizon.brbrStep aboard FREE TIME, your 50-foot floating suite in Key West. Two ensuite staterooms, a sun-soaked salon and a private deck made for sunrise, coffee or champagne sunsets.Docked in a premier marina with resort-style perks, this yacht redefines luxury travel-it's not a stay, it's a story you will tell for years.brbrThe SpacebrWelcome to FREE TIME, where adventures and elegance meet the ocean breeze.brThis 50-foot yacht features two hotel style staterooms with queen beds, en-suite baths, and a panoramic salon designed for connection and comfort. Professionally detailed after every voyage, your floating villa includes access to pools, fitness and a marina shuttle to Duval Street. Whether you crave serenity or spontaneity, every moment aboard feels cinematic -Key West at its finestbrbrSnorkel crystal -clear waters, relax at iconic sandbars, or head out for a fishing adventures-all easy arranged. Elevate your stay with optional grocery provisioning and onboard food & beverage services so everything is stocked and ready before you arrive. Add-on experiences include sunset cruising, celebrations and custom moments designed to make your time on the water seamless, indulgent and unforgettable.brbrGuest AccessbrAs marina-based experience professionals, we specialize in curating exclusive waterfront upgrades for our guests. Ask about optional VIP add-ons such romance packages, yacht enhancements, photo shoots local marina experiences. These can be arranged separately after booking on line. Guests of FREE TIME Charters enjoy VIP marina privileges:br*Full access to pools, restaurants and gym.br*Complimentary parkingbr*Free shuttle to and from downtownbr*Dock and gate codes sent before arrivalbrbrThis is not a standard stay...brbrEvery FREE TIME charters reservation is prepared intentionally. After booking, guest receive access to our Harbor desk and a brief pre-boarding preference form - allowing us to prepare arrival details, onboard comfort and complimentary welcome touches in advance.brbrCompletion of the pre-boarding preferences ensures luggage assistance, premium water and light snacks and a professionally prepared yacht upon arrival. brbrFor guests who wish to elevate their stay further, select enhancements may be arranged in advance after booking, including priority boarding, brand new linen preparation, romantic or celebration setups, extended departure when available. Access to select on-the-water excursions, or luxury day charter.brbrEverything is prepared intentionally. Nothing is rushed.brbrOther things to notebrThis is a docked luxury yacht stay; the vessel remains at the marina unless a private charter or sunset cruise is arranged in advance as a separate experience.brbrTo preserve the yacht's refined interiors, guests are kindly ask to remove shoes while onboard.brbrEnjoy a relaxed departure-no cleaning required. Simply gather personal belongings and secure the yacht upon exit.brbrGuest enjoy complimentary parking, access to the resort-style pool, private beach, tiki huts, lookout deck complete with picknick tables and Adirondack chairs and gym all located within the marina property.brbrCheck-in begins after 3:00pm / Check-out by 10:00ambrbrThis is a luxury yacht stay, not a traditional hotel room. Guests should be comfortable around boats and marina settings.brbr*The yacht remains docked at the marina and can be charter for excursions .br*Marina ambiance includes gentle movement, dock activity and occasional marine sounds-part of the authentic waterfront experience.br*Access involves walking on docks and stepping on board; mobility comfort is important .br*Quiet hours are respected in the marina 11:00pm no noise or loud music to ensure a peaceful stay for all guests.br*No parties or unregistered visitors without prior approval.br*Weather and marine conditions may occasionally effect dock access or marine amenities .br*Detailed arrival instructions, parking info and onboard guidance will be provided prior to check-in.

Bed

Bath

Sleeps

$213.7

/ Nightly

Apartment

Renovated 2BR/2BA Condo • Pool • Spa • Tennis • Walk to Smathers Beach!

Key West, Florida, United States

This beautiful 2 bed, 2 bath condo is newly listed after a complete renovation, including all new furniture and improvements. It is located in the quiet, professionally managed Salt Ponds community. The condo is on the third level with views of the Salt Ponds (no afternoon sun). Amenities include large pool, heated spa, and lighted tennis courts, with a 10-minute walk to Smathers Beach. The community is a short drive, or bike ride, to Old Town Key West. Close enough to enjoy but away from the unwanted commotion. As a new listing, it is offered at a reduced rate.

Bed

Bath

Sleeps

$215.89

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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!

Bed

Bath

Sleeps

$192.25

/ Nightly

Condo

ADRIFT IN KEY WEST at the Truman Annex in Key West

Key West, Florida, United States

Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely transformed. Fully appointed, sleek kitchen with all new appliances (oven/microwave combo unit), lighted kitchen drawers, washer/dryer in unit, comfortable private back patio oasis with comfortable furniture for lounging and entertaining. and outdoor Shower. End unit, bike rack right outside, gated community. Conveniently located in the Shipyard Complex of the Truman Annex just steps from the active lifestyle of Duval Street, shopping, dining, and night life. Also steps from Mallory Square for gorgeous sunset views and the new Truman Waterfront Park. Assigned off street parking for 1 vehicle. brPlease note: This property will require a minimum of a 28 night stay.

Bed

Bath

Sleeps

$356.1

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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....

Bed

Bath

Sleeps

$431.28

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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

Bed

Bath

Sleeps

$527.19

/ Nightly

Condo

Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.brbrThe property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.brThis spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensuite full bathroom with shower and bath tub. The guest bedroom features a queen bed with wood flooring. The condo also features a full kitchen, with a full refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HD TV, a dining area and access to a private patio. This is a two-story condo and the bedrooms are upstairs.brbr*Must climb stairs — Stairs required to access the unit, Stairs may be required to access bedroomsbrbrGuest must be 25 yrs old to rent and check-in to this unit.brbrUnits are assigned in seven night increments, multiple week stays may be booked, room moves may be required.brOccupancy limits are strictly enforced.brbrNo RVs, campers or mobile homes may be parked on the premises. Parking is limited to two (2) vehicles per unit.brbrWelcome Center hours of operation are: Sunday to Thursday 9am – 5pm and Friday/Saturday 8am – 10pm. Late arrivals must call the welcome center for arrangements.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. Towel Exchange is not available.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.

Bed

Bath

Sleeps

$235.0

/ Nightly

Apartment

Beautiful Upper Duval - Uptown - 2 bedroom Condo

Key West, Florida, United States

Location, Location!!Welcome to our Key West Condo! This beautiful Upper Duvalcondo is walkable to everything in Key West. Known as the Uptown of Old Town Key West and theelegant end of Duval.What we love is that you can be in the excitement of Duval St, on South beach, at the Southernmost Point, or at the free MLK Pool, in just minutes going either direction. The location could not be more perfect!Our goal is that you feel at home here - the condo is stocked with everything you need. Sip a cup of coffee on the balcony, or simply walk around to enjoy the City!brThe condo is close to everything, and peaceful at the same time. Perfect for a family or up to 3 couples (3rd bed is in the pull-out couch with memory foam mattress). 2 full bathrooms! The kitchen is fully stocked with all essentials.brWe are available by phone or textanytime. Please feel free to reach out. Our contact info is in the information packet we will send out once it's time for your stay.brThe neighborhood is wonderful, right off the southern part of Duval St., right next to Banana Cafe! About a 5 minute walk and you're either at the free MLK ocean view pool, the Southernmost Point , or South Beach. Enjoy bars, restaurants, museums, and shopping just by walking!brOur favorite way to get around is by moped! You can park right in front of the unit as well.See our guidebook for local vendors who rent out mopeds and golf carts. There are also a lot of bike rental options. You will not need a car!brWe want to ensure your stay is fabulous! Please contact us if you need anything at all.

Bed

Bath

Sleeps

$326.25

/ Nightly

Condo

Tropical Paradise In Key West-Coconut Beach Resort - Avail 4/24/27 to 5/1/27

Key West, Florida, United States

Book it before it's gone! 7 Day rental - available from Saturday 4/24/27 to Saturday 5/1/27 only.brbrCozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, large pool, and sun deck, this exclusive property is a paradise, complete with lush tropical landscaping everywhere you look. This unit itself was completely renovated recently, has a private entrance, faces the street, and is well appointed and comfortable. It features a king-size bed, a full bath and central air conditioning. Step out onto your own private balcony, where you can relax and listen to the breeze through the palm trees. The hidden closet provides some unexpected surprises too, including a microwave, small refrigerator, even a coffee maker. You’ll spend your days where everyone does, around the magnificent common area facing the ocean, where the trees and tropical foliage abound. The pool area is amazing, with plenty of places to relax – either right in the sun, or in your own shady spot. The heated pool itself is magnificent, and you’ll love the swimming. You’ll want for nothing – there’s a hot tub out there, gas grills, rest rooms, even a water cooler to keep you hydrated. You can even enjoy your own private sunsets, right on the premises if you like. CBR is a stunning, beautiful place and it’s a short walk (or bike) to all the fun on Duval Street.brbrThis is a Timeshare Resort, and I’m the owner of this specific week. This is a Saturday to Saturday rental. Check-in time is Sat at 4pm (you can sometimes get in earlier), and you’ll need to check out on the following Saturday by 10am. There is a mid-week housekeeping crew that will tidy things up as well – no extra charge.brbrI’ve posted some of my own personal photos, and have been an owner at Coconut Beach Resort for over 20 years. Check out more photos on CBR’s site - coconutbeachresort . combrbrRent elsewhere for MUCH MORE per night, and you won’t get the amenities that CBR has. The dates and price are not flexible, and this unit is a 7 Day rental only, and available from Saturday 4/24/27 to Saturday 5/1/27 only.

Bed

Bath

Sleeps

$1128.84

/ Nightly

Private Vacation Home

PERFECTION...STEPS FROM DUVAL ~

Key West, Florida, United States

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.

Bed

Bath

Sleeps

$2029.65

/ Nightly

Private Vacation Home

CLASSIC KEY WEST - Grand home in Old Town location

Key West, Florida, United States

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.

Bed

Bath

Sleeps

$3092.17

/ Nightly

Private Vacation Home

WATSON HOUSE GRAND ESTATE on Simonton St

Key West, Florida, United States

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.

Bed

Bath

Sleeps

$309.38

/ Nightly

Hotel Resort

Hyatt Vacation Club in Key West- Studio

Key West, Florida, United States

Key West at its best. Hyatt Sunset Harbor resort directly overlooking the gulf. Just 1 block to Mallory Square and the world famous nightly sunset celebration. 2 blocks to Duval Street and all the famous Key West attractions: Sloppy Joe's, Hemmingway's House, Hogs Breath Saloon and countless shops, galleries, cafes and restaurants. Working harbor directly outside the property. Cruise ships pull up across the harbor in the morning and leave before sunset. Try the Watersports Activities-Jet Ski, Snorkel, Diving, Parasailing or Sunset Sail trips, all located dockside next to the resort.brThe property has a beautiful deck area with a large heated pool, hot tub, swing set, chaise lounges, barbeques and two pergolas all overlooking the harbor.brGarage parking is available across the street at ~ $10/day but a car is not necessary, walk to almost everything worth doing in Key West. Concierge, on-site laundry, child care, cribs and high chairs upon request, DVD rental. Enjoy additional facilities and amenities at the nearby Hyatt Centric Key West Resort & Spa.brHyatt will charge up to $80 in fees for 4 night staysbrContact Mike M directly @ 954 600-556fourbrbrThis listing is also available on Redweek although the fees are higher on Redweek.brI have been a member of Redweek since 2017 and have bought, sold and rented 30+ times with 100% satisfaction. Redweek verification a/o payment can be added upon request.

1

Bed

1

Bath

2

Sleeps

$314.6

/ Nightly

Condo

The Andros | Incredible Views w/ Shared Pool

Key West, Florida, United States

The Andros | Incredible Views w/ Shared PoolbrbrEscape to The Andros, a serene, beautifully designed 2-bedroom, 2-bath condo nestled in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the beach with its stunning aqua-blue waters and loungers, this charming retreat offers the perfect mix of relaxation and adventure. Whether you're soaking in the hot tub, exploring the vibrant attractions of nearby Duval Street, or unwinding on your private balcony with breathtaking sunset views, The Andro's is your ideal Key West getaway.brbrThe Ambiance:brStep into The Andros and experience a harmonious blend of modern comfort and tropical charm. This inviting fourth-floor condo accommodates up to six guests, featuring a king-sized bed in the master bedroom, a queen-sized bed in the second bedroom, and a queen pullout sofa in the living area for extra guests. The fully equipped kitchen makes cooking a pleasure, while the private balcony provides exquisite views of the surrounding salt marshes. With central air conditioning, free WiFi, and cable TV, Butterfly Nest offers all the comforts of home in a serene island setting.brbrGuest Access:brArrive with ease through our contactless check-in process, where you'll receive a personalized access code three days before your stay. During your visit, take advantage of the many shared amenities, including:brbr- A heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbr- The unit is easily accessible via stairs or elevator, ensuring convenience for all guests.brbrLocation Highlights:brThe Andros is perfectly situated within the peaceful Sunrise Suites Resort, just 10 minutes from the lively restaurants, art galleries, and nightlife of Duval Street. For breathtaking evening entertainment, visit the nearby Sunset Celebration at Mallory Square. The resort itself offers a corner store, spa, and scenic trails, while the Key West airport is conveniently located nearby for stress-free travel.brbrGetting Around:brEnjoy the convenience of one private parking spot under the building (spot #155), with additional parking available on a first-come, first-served basis. Explore Key West by bike, scooter, golf cart, or even on foot, with many attractions within walking distance. Rideshare services and taxis are also readily available for longer trips.brbrOther Things to Note:br- Pets are welcome (40 lbs maximum per pet) with a $20 per pet, per night fee. Please let us know in advance if you'll be bringing pets.br- A private stackable washer/dryer is available in the unit for added convenience.br- The unit is located near the airport, offering easy accessibility.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.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.

2

Bed

2

Bath

6

Sleeps

$305.76

/ Nightly

Condo

The Butterfly Nest | Newly Updated w/ Shared Pool

Key West, Florida, United States

The Butterfly Nest | Newly Updated w/ Shared PoolbrbrEscape to The Butterfly Nest, a serene, beautifully designed 2-bedroom condo located in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the pristine beach and a quick 10-minute ride to the lively Duval Street, The Butterfly Nest offers the perfect blend of relaxation and adventure. Whether you're basking by the pool, exploring local attractions, or enjoying the comforts of this charming retreat, The Butterfly Nest promises an unforgettable Key West experience.brbrThe Ambiance:brStep into The Butterfly Nest and immerse yourself in a cozy, thoughtfully decorated retreat that exudes comfort and charm. The condo features a master bedroom with a king-sized bed and a private ensuite bathroom, while the second bedroom offers a queen-sized bed with convenient access to the hall bathroom. A plush blue sofa in the living room converts into a queen-sized sleeper, making the space perfect for up to six guests. The open-concept living area invites relaxation, whether you're enjoying a meal prepared in the fully equipped kitchen, lounging on the couch with cable TV, or stepping out onto the private balcony with seating for four. With central air conditioning and all the comforts of home, The Butterfly Nest is the ideal space to unwind and recharge.brbrGuest Access:brEnjoy a seamless arrival with our contactless check-in process—guests receive a personalized access code three days before arrival. During your stay, take advantage of Sunrise Suites' exceptional shared amenities, including:brbr- Communal heated pool and hot tubbr- Tennis courtbr- Scenic walking paths and biking trailsbr- The unit is easily accessible via stairs or elevator, ensuring convenience for all.brbrLocation Highlights:brThe Butterfly Nest is ideally located in the peaceful Sunrise Suites community, offering easy access to Key West's best attractions. The beach, with its turquoise waters and loungers, is just a mile away, while the vibrant restaurants, bars, and nightlife of Duval Street are only a 10-minute drive. Key West International Airport is also conveniently close, making travel a breeze.brbrGetting Around:brThe condo includes parking for your convenience. Bike, scooter, and golf cart rentals are readily available nearby, allowing you to explore Key West's charming streets with ease. Taxis and rideshare services are also a great option for getting around.brbrOther Things to Note:br- Pet-Friendly Policy: Pets are welcome!br- Maximum weight: 40 lbs per petbr- $20/night per pet (2-pet maximum)br- Please notify us if you plan to bring your furry friend!br- A private stackable washer/dryer is available in the unit for added convenience.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.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.

2

Bed

2

Bath

6

Sleeps

$509.36

/ Nightly

Private Vacation Home

Sea Esta Suite | Located On Iconic Duval w/ Pool

Key West, Florida, United States

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.

Bed

Bath

Sleeps

$288.9

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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…

Bed

Bath

Sleeps

$734.4

/ Nightly

Apartment

Sailfish Suite on Duval

Key West, Florida, United States

Summary:brbrBeautifully renovated 2-bedroom, 2-bathroom apartment with shared pool on Duval StreetbrbrbrbrThe Space:brbrWelcome to the Sailfish Suite, your tropical retreat located in the heart of Key West! Situated on lively Duval Street, this beautifully renovated 2-bedroom, 2-bathroom apartment combines comfort with the charm of its original character, offering an unforgettable stay, brbrbrbrKey Features:brbrbrbr• 2 Bedrooms: Each bedroom features a king-sized bed. The back bedroom boasts a private en suite bathroom. While the front bedroom is separated by a connecting balcony, ideal for relaxing with a coffee or cocktail, and shares the bathroom with the living room/kitchenette.brbrbrbr• 2 Bathrooms: Both bathrooms are well-appointed with fresh linens and essentials.brbrbrbr• Kitchenette: allows you to prepare meals.brbrbrbr• Shared Pool Access: Just steps from the suite, the small shared pool offers a tranquil escape, perfect for cooling off after a day exploring Key West.brbrbrbrThe Sailfish Suite has undergone an extensive renovation, maintaining its unique original charm while incorporating all the modern amenities you need for a comfortable stay. Perched on Duval Street above the popular Grand Cafe, you’ll find yourself in the heart of Key West’s energy. From renowned restaurants and boutique shopping to galleries and nightlife, everything you need is just outside your door. brbrbrbrDuval Street is one of the most iconic and vibrant streets in the United States, renowned for its lively atmosphere, rich history, and colorful culture. Stretching just over a mile from the Gulf of Mexico to the Atlantic Ocean, Duval Street is the heartbeat of Key West, offering something for everyone. What makes it so special brbrbrbrEnergetic Atmosphere: Duval Street buzzes with life day and night, featuring live music, street performers, and a festive ambiance. It’s a hub for both locals and tourists who come to soak in the unique island vibe.brbrbrbrBars and Nightlife: Known as a mecca for nightlife, Duval Street boasts legendary bars like Sloppy Joe’s, Hog’s Breath Saloon, and The Green Parrot. Whether you’re looking for a lively pub crawl or a cozy cocktail spot, this street delivers.brbrbrbrEclectic Shopping: The street is lined with quirky boutiques, art galleries, and souvenir shops. You’ll find everything from locally crafted goods and tropical apparel to fine art and kitschy mementos.brbrbrbrCulinary Delights: Duval Street is a food lover’s paradise. Restaurants range from casual seafood shacks to upscale dining establishments, offering fresh seafood, Cuban-inspired dishes, and the famous Key lime pie.brbrbrbrHistorical Landmarks: Key West’s rich history is woven into Duval Street. Landmarks like the Ernest Hemingway Home and Museum, St. Paul’s Episcopal Church, and the Key West Lighthouse are nearby, providing a glimpse into the past.brbrbrbrFestivals and Events: Duval Street plays host to some of Key West’s biggest events, such as Fantasy Fest, the Hemingway Days Festival, and the Conch Republic Independence Celebration. These events transform the street into a vibrant celebration of local culture and creativity.brbrbrbrTropical Charm: Flanked by colorful, historic buildings, lush palm trees, and the occasional rooster wandering by, Duval Street embodies the laid-back yet lively spirit of Key West.brbrbrbrWhat to Expect on Duval Street: Whether you’re strolling in the daytime to shop and sightsee or embracing the spirited nightlife, Duval Street offers a little bit of everything. Its eclectic blend of entertainment, dining, and history makes it a must-visit destination for anyone exploring the Florida Keys.brbrbrbrPlease note: There's no parking available on site, so you'll need to find street parking in the neighborhood or park in one of the paid lots that permits overnight or 24-hour parking. No smoking. No pets.

2

Bed

2

Bath

4

Sleeps

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