Key West Homes with Furnished

Key West Homes with Furnished

Welcome to Key West, Florida—a vibrant island paradise nestled in Monroe County, renowned for its stunning sunsets, lively culture, and rich history. As the southernmost point in the continental United States, Key West boasts a unique charm that draws visitors and residents alike to its sun-kissed shores and laid-back lifestyle.

In Key West, you’ll find an eclectic mix of historic architecture, from colorful conch houses to modern beachfront properties, all infused with the island’s distinctive character. Whether you’re seeking a cozy cottage or a luxurious waterfront estate, the real estate market here offers a variety of homes that cater to diverse tastes and budgets.

One of the standout features of many homes in Key West is that they come fully furnished, making your transition to island life seamless and stress-free. Imagine stepping into a beautifully decorated space that reflects the vibrant colors of the surrounding landscape, complete with comfortable furnishings and stylish decor. These homes are not just places to live; they are sanctuaries where you can unwind and embrace the island’s relaxed vibe.

Key West is also known for its outdoor activities, from snorkeling in crystal-clear waters to exploring the lush landscapes of the Dry Tortugas National Park. With a bustling arts scene, lively nightlife, and an array of dining options, there’s always something to do in this enchanting locale.

Discover the magic of Key West real estate today, where furnished homes await to welcome you to your new island life!

Newest Key West Homes with Furnished

$2,400,000
3 Beds ⋅ 3 Baths ⋅ 621218 MLS
Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

2623 Gulfview Dr, Key West
$5,400,000
6 Beds ⋅ 7 Baths ⋅ 621215 MLS
Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate luxury island retreat or multi-generational estate. Verdant foliage frames the wrap-around front porch of the front cottage, inviting you to sit back and enjoy quintessential island living. Inside, sky-lit vaulted ceilings with exposed wooden beams pour warm sunshine across white-painted walls and rich wood floors. The light-filled layout centers around an enchanting cottage kitchen filled with warmth and timeless charm that flows seamlessly into the living space and guest half bath. Three bedrooms-each featuring its own private ensuite bath-offer exceptional comfort. Floor-to-ceiling glass draws you out to an outdoor dining area and a sparkling heated pool nestled among vibrant gardens. Wander through the botanical grounds to the rear house, a custom-crafted two-story sanctuary built in 2016. Showcasing exquisite Hickory hardwood floors, whitewashed Cypress interior walls, and slate-tiled baths, this home balances coastal elegance with high-end luxury. The chef's kitchen boasts an elite ILVE range and custom cabinetry, flowing into open living quarters that slide open to the backyard oasis. The main floor offers versatile living with a guest suite that double-functions as a private home office with a built-in Murphy bed. Upstairs, a Craftsman staircase leads to a secondary guest suite with an ensuite bath and a sprawling primary retreat, complete with an oversized spa bath and a private balcony overlooking the second heated waterfall pool. Do not miss this rare chance to own one of Old Town's premier dual-home properties, complete with dedicated off-street parking for two cars.

613 Margaret St, Key West
$1,890,000
2 Beds ⋅ 3 Baths ⋅ 621199 MLS
Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Listed on the National Register of Historic Places and awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a sundeck with a covered dining area and extra lounging space to entertain. A Pool with water feature and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. The house has some monthly vacation rental history and is sold furnished (some personal pieces & all art work excluded)!

516 Elizabeth St, Key West
$1,225,000
1 Beds ⋅ 1 Baths ⋅ 621189 MLS
A TRANSIENT LICENSED vacation rental located in the heart of Old Town Key West, the X flood zone and just 2.5 blocks from world famous Duval Street. The transient license allows for nightly rentals. A savvy investor could pounce on this rare opportunity to own a well-managed income producing property with excellent history & immediate income. Unit 6, aka Hidden Oasis, is 1 of only 11 units within the coveted enclave known as The Colony which features a large heated community pool, shared off-street parking and a gated entry to the pool area & the unit, all managed by the HOA. Hidden Oasis has a prime location within the community tucked into the back left corner with an entry deck and an abundant private rear deck that includes exclusive use of umbrella seating for 4, a propane grill, a full size washer & dryer and an outdoor shower stall. This well maintained unit has an updated kitchen, bathroom and mini-split air conditioning. The living area is light & airy with transom windows, vaulted ceilings and a well-appointed open kitchen. The spacious bedroom features a king sized bed, tropical décor and access to the front deck. Pride of ownership is obvious when you review the recent history of this owner managed HOA. The community pool was resurfaced in 2021, all buildings had new metal roofs installed in 2023 and all buildings were termite tented August 2026. Take advantage of this rare opportunity for an excellent Key West investment with an owner use option. With local property management & HOA management already in place, Hidden Oasis makes for an immediate complete turnkey 'hands-free' vacation rental ownership choice for a remote owner. Sold furnished with future bookings.

714 Olivia St Unit # 6, Key West
$1,395,000
2 Beds ⋅ 4 Baths ⋅ 621163 MLS
NEW LISTING IN OLD TOWN WITH OFF STREET PARKING! This Old Town investment property comes fully furnished so you can move right in or start renting immediately. It is a legal duplex with two units, each having one bedroom and one and a half bathrooms but could easily be converted to a single family home. Located on a fenced corner lot in Old Town, it's just blocks from Duval Street, making it very convenient for dining, shopping, nightlife and enjoying the Key West sights The home has updated kitchen and baths, ductless AC units, hardwood floors, vaulted ceilings, and skylights. It's a perfect mix of modern style and classic Keys architecture. Live in one unit and rent out the other, have a dedicated private guest space, or use both to generate income. Each unit has its own private outdoor area and laundry. There is a welcoming front porch perfect for morning coffee. Desired X Flood Zone!

709 Olivia St, Key West
$1,395,000
2 Beds ⋅ 4 Baths ⋅ 621159 MLS
NEW LISTING IN OLD TOWN WITH OFF STREET PARKING! This Old Town investment property comes fully furnished so you can move right in or start renting immediately. It is a legal DUPLEX with two units, each having one bedroom and one and a half bathrooms. Located on a fenced corner lot in Old Town, it's just blocks from Duval Street, making it very convenient for dining, shopping, nightlife and enjoying the Key West sights The home has updated kitchen and baths, ductless AC units, hardwood floors, vaulted ceilings, and skylights. It's a perfect mix of modern style and classic Keys architecture. Live in one unit and rent out the other, have a dedicated private guest space, or use both to generate income. Each unit has its own private outdoor area and laundry. There is a welcoming front porch perfect for morning coffee. Desired X Flood Zone!

709 Olivia St, Key West
$995,000
2 Beds ⋅ 2 Baths ⋅ 621152 MLS
Exquisite, turnkey resort living awaits in this fully furnished 2-bedroom, 2-bathroom oceanfront condominium, offering an effortless transition into Key West luxury just steps from world-famous Smathers Beach. Tucked away in a quiet oceanfront enclave, you are just minutes from Old Town, world-class dining, marinas, and the airport. Inside, high-end interior upgrades feature rich wood-grain LVP flooring through the main living areas and bedrooms, complemented by elegant large-format porcelain tile in the renovated bathrooms. The kitchen and dedicated wet bar showcase polished marble countertops, custom white shaker cabinetry, stainless steel appliances, and built-in wine storage. Light-filled open living and dining spaces flow seamlessly through hurricane impact glass sliders onto a massive 38-foot private balcony framing lush tropical greenery and partial ocean views. The primary suite boasts generous closet space, an updated vanity, and a custom walk-in shower with a frameless glass enclosure and direct balcony access. Key Property Details: Parking & Storage: Assigned covered garage parking spot plus a private locked storage locker located directly in front of your vehicle. Turnkey Ready: Sold complete with all designer furnishings, artwork, flat-screen TVs, linens, and housewares for instant occupancy. Resort Amenities: On-site sunning beach, heated oceanfront Olympic-size pool, jacuzzi, saunas, a brand-new fitness center, 3 lighted tennis courts (including 1 clay court), BBQ picnic areas, and lush botanical gardens. Effortless Ownership: HOA fees cover building insurance, exterior maintenance, water, cable/high-speed internet, and fully funded reserves ($20k assessment paid). Strong rental track record ($72k+ net annual yield).

1800 Atlantic Blvd Unit 325C, Key West
$9,495,000
3 Beds ⋅ 3 Baths ⋅ 621128 MLS
Rare Opportunity: The Only Home For Sale on Crescent Beach, Sunset Key Welcome to 11 Sunset Key Drive -- a fully renovated retreat on the most exclusive private island in the Florida Keys, and the only property currently available on Crescent Beach. Accessible exclusively by private ferry, Sunset Key offers a rare combination of true seclusion and effortless proximity to Old Town Key West, just minutes away. Completely renovated in 2018 with over $1.7 million invested, this 3-bedroom, 2.5-bath, close to 3,000-square-foot home was rebuilt for easy island living: hurricane-impact doors and windows, an updated roof, all-new electrical and white oak engineered wood flooring, a new interior fire suppression sprinkler system, and a full exterior and interior repaint. The kitchen centers on a Sub-Zero refrigerator, new stainless appliances, new countertops and custom cabinetry, while the private pool/spa was rebuilt down to the plumbing with new handcrafted and hand painted tile, equipment, heater, LED lighting and all app-controlled. Fully furnished by Restoration Hardware and ready to move into exactly as it is. Ownership here includes access to an oceanfront restaurant, full-service spa, fitness center, tennis courts, and private beaches -- all steps from the front door. Sunset Key holds only a handful of homes, and Crescent Beach holds fewer still. Schedule your private showing today. See you soon!!!

11 Sunset, Key West
$2,599,000
3 Beds ⋅ 2 Baths ⋅ 621061 MLS
Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. Enjoy an open floor plan where the kitchen is truly the heart of the home complete with top of the line stainless Thermador appliances, quartz countertops and timeless cabinetry with a central island perfect for entertaining! Matching custom cabinetry extends into the quaint living room space offering thoughtful built in storage and a beautiful entertainment backdrop. Reclaimed Dade County pine has been lovingly restored into an accent wall rich with history and elegance. Vaulted ceilings finished in grasscloth and wood beams are found in every room of this home. Enjoy 2 spacious ensuite luxury bathrooms and a gorgeous poolside outdoor shower. Low maintenance composite decking surrounds the home and pool area that accommodates dining and lounging in or out of the pool with a sun shelf and waterfall. Lets not forget the darling covered front porch that welcomes you to this quiet lane cottage also offering off street parking. Carsten Lane is a one way driving lane stretching only one block located in the heart of Old Town known for its peaceful and private setting!

812 Carsten Ln, Key West
$819,000
1 Beds ⋅ 1 Baths ⋅ 621059 MLS
This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Ideally situated on a quiet one-way street, this tropical retreat is just a short stroll from some of Key West's best boutiques, bakeries, art galleries, restaurants, and gourmet food markets. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West
$3,700,000
3 Beds ⋅ 4 Baths ⋅ 620985 MLS
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

530 Catherine St, Key West
$649,000
2 Beds ⋅ 2 Baths ⋅ 620917 MLS
Beautiful ''Bungalow'' style townhome in the highly sought after Key West Golf Club. Professionally landscaped yard and new paver walkway with landscape lighting and irrigation system invites you into this fully furnished 2 bedroom and 1.5 bath home with quartz countertops, stainless appliances and brand new 2026 central A/C. Relax on the screened in porch over looking the fairway of the Rees-Jones designed 18 hole Golf Course. KWGC community includes 2 heated swimming pools, fitness center, butterfly gardens and 24 hour gated security.

30 Kingfisher Ln, Key West
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