Key West Homes with Guest Quarters Exterior features

Key West Homes with Guest Quarters Exterior features

Welcome to Key West, Florida, a tropical paradise that perfectly blends vibrant culture, stunning natural beauty, and a laid-back lifestyle. Nestled in Monroe County, this enchanting city is renowned for its picturesque sunsets, lively nightlife, and rich history, making it a sought-after destination for both residents and visitors alike.

Key West is not just about breathtaking beaches and eclectic charm; it’s also a haven for unique real estate opportunities. Among these, homes with guest quarters stand out as a fantastic option for those seeking versatility and additional space. Imagine a property where you can host family and friends, or even generate rental income, all while enjoying the island's breathtaking views and warm breezes.

These homes often feature beautifully designed guest quarters on the property, providing privacy and comfort for visitors. Whether it’s a cozy studio or a spacious apartment, these quarters are perfect for accommodating guests or setting up a home office. Many properties boast stunning exterior features, including lush tropical landscaping, private pools, and outdoor living spaces that allow you to soak in the island sun.

The allure of Key West extends beyond its real estate; it’s about embracing a lifestyle filled with adventure. From water sports and fishing to exploring the vibrant art scene and indulging in delicious seafood, there’s always something to do. With its unique blend of charm and opportunity, Key West is not just a place to live; it’s a place to thrive. Explore the possibilities of owning a home with guest quarters in this idyllic city and start your journey in paradise today!

Newest Key West Homes with Guest Quarters Exterior features

806 Truman Ave, Key West
$5,365,000
5 Beds ⋅ 6 Baths ⋅ 621899 MLS
Discover The Victoria House, a distinctive historic Key West residence with a transient license where timeless architectural charm meets the relaxed elegance of island living. Offered furnished at $5,365,000, this remarkable property at 806 Truman Avenue features five bedrooms, five full bathrooms, and two half bathrooms across the main residence and private pool house. Classic Victorian-inspired architecture, inviting covered porches, beautiful wood floors, vaulted beadboard ceilings, and lush tropical landscaping create an atmosphere of warmth and sophistication. Thoughtfully arranged across three levels, the main residence features two second-floor primary suites with king beds, en-suite bathrooms, and direct access to private outdoor spaces. The third floor offers a queen bedroom, a spacious two-queen bedroom suite, and a charming loft sitting area. The separate pool house provides additional privacy with a king bedroom, en-suite full bathroom, and direct access to the spectacular pool courtyard. Designed for effortless indoor-outdoor living, the tropical courtyard features a private swimming pool, spa, expansive sun decks, covered outdoor dining, upper-level balconies, and a distinctive spiral staircase. Mature palms, brick walkways, and classic white picket fencing enhance the property's unmistakable Key West character. Whether entertaining guests, relaxing beside the pool, or enjoying a quiet morning on the covered front porch, The Victoria House offers an exceptional opportunity to experience the beauty, character, and lifestyle of historic Key West. Offered furnished for a seamless transition to island living.

806 Truman Ave, Key West
923 Fleming St, Key West
$5,300,000
7 Beds ⋅ 6 Baths ⋅ 621882 MLS
A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

923 Fleming St, Key West
3801 Flagler Ave, Key West
$2,229,000
3 Beds ⋅ 3 Baths ⋅ 621725 MLS
Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3801 Flagler Ave, Key West
813 Thomas St, Key West
$3,895,000
4 Beds ⋅ 3 Baths ⋅ 621693 MLS
Steps From Duval. Worlds Away. Morning coffee on the wraparound porch. An afternoon swim beneath the waterfall. Dinner under the stars. At 813 Thomas Street, every day feels like the best kind of Key West getaway. Set on a rare double lot in Flood Zone X and completely renovated in 2025, this island-contemporary residence pairs a 3-bedroom, 2-bath main home with a brand-new 1-bed, 1-bath guest cottage, giving family and friends a private retreat of their own. Inside, soaring ceilings, sun-drenched living spaces, and hardwood floors set an elegant tone. The chef's kitchen is the showpiece, with custom cabinetry, a sculptural quartz waterfall island, and a full suite of Thermador stainless steel appliances delivering professional-caliber performance with refined style. Whether it's a quiet breakfast or a dinner party for a crowd, this kitchen is ready for it. The entire second floor belongs to the primary suite, with a private balcony, walk-in closet, and spa-style bath featuring a deep soaking tub, double vanity, and separate shower. Impact French doors open to the outdoor living spaces. A motorized pergola covers the alfresco dining area and grill station or opens to the sky at the touch of a button. More than 500 square feet of decking wraps a 15' x 22' heated completely new saltwater pool with a Cosentino Dekton waterfall, surrounded by lush tropical landscaping and an outdoor shower. Gated driveway with off-street parking for two completes this move-in ready offering. The location is pure Old Town: stroll to Blue Heaven for brunch, tour the Hemingway Home and the Key West Lighthouse, catch the sunset at Fort Zachary Taylor, snap a photo at the Southernmost Point, or explore Duval Street and Bahama Village, all within walking distance. Homes like this in the heart of Old Town are rarely available. Schedule your private showing today!

813 Thomas St, Key West
830 Johnson Ln, Key West
$1,500,000
2 Beds ⋅ 1 Baths ⋅ 621685 MLS
Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Neighboring property at 832 Johnson Lane is also available for sale.

830 Johnson Ln, Key West
830 Johnson Ln, Key West
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 621684 MLS
Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a storage loft. The guest house sits at the rear of the property and features 1bd/1ba, kitchen, living room and loft. There is a spacious open area between the 2 structures finished in composite decking currently set up for outdoor dining and living or the ideal space for the addition of a pool. Bright and airy with vaulted ceilings throughout and multiple sets of French doors. Enjoy a newly renovated bathroom in the main house. Truly a great opportunity to dress up and expand upon a charming historic property. Or, enjoy the rustic charm of two cottages complete with kitchens on a peaceful one way Old Town driving lane. Offered fully furnished with professional management in place and future bookings to convey. Property is considered a legal duplex. Neighboring property at 832 Johnson Lane is also available for sale.

830 Johnson Ln, Key West
720d Simonton St, Key West
$4,950,000
4 Beds ⋅ 4 Baths ⋅ 621632 MLS
DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

720d Simonton St, Key West
1311 Truman Ave, Key West
$6,449,000
7 Beds ⋅ 8 Baths ⋅ 621544 MLS
Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West
1221 Ashby St, Key West
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 621518 MLS
Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

1221 Ashby St, Key West
317 Whitehead St, Key West
$6,895,000
6 Beds ⋅ 7 Baths ⋅ 621466 MLS
The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West
32 Sunset, Key West
$12,500,000
6 Beds ⋅ 7 Baths ⋅ 620770 MLS
A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, Key West
3712 Duck Ave, Key West
$849,000
3 Beds ⋅ 3 Baths ⋅ 620501 MLS
Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3712 Duck Ave, Key West
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