Key West Homes with Yes Pets allowed

Key West Homes with Yes Pets allowed

Welcome to Key West, Florida—a tropical paradise that offers a unique blend of vibrant culture, stunning natural beauty, and a laid-back lifestyle that residents cherish. Nestled in Monroe County, Key West is the southernmost point in the continental United States and is renowned for its breathtaking sunsets, crystal-clear waters, and rich history. This charming island city is a haven for artists, writers, and those seeking a tranquil escape from the hustle and bustle of everyday life.

Key West boasts a variety of homes that cater to a diverse range of lifestyles, particularly for pet lovers! Many properties in this sun-soaked paradise welcome furry friends, ensuring that your pets can enjoy the island life just as much as you do. Imagine strolling with your dog along the picturesque streets lined with swaying palm trees or enjoying a beach day at one of the pet-friendly parks.

Whether you're searching for a cozy cottage, a modern condo, or a luxurious waterfront estate, Key West offers something for everyone. With a vibrant real estate market, you can find homes that not only accommodate your family but also your beloved pets. The welcoming community, coupled with the island's stunning environment, makes it a perfect place for both you and your four-legged companions to thrive.

Discover your dream home in Key West and embrace the enchanting lifestyle that awaits you and your pets in this idyllic coastal retreat!

Newest Key West Homes with Yes Pets allowed

1119 Johnson St, Key West
$5,650,000
3 Beds ⋅ 4 Baths ⋅ 621891 MLS
Discover timeless design and effortless indoor-outdoor living in this custom-built 4-bedroom, 3.5-bath residence in Key West's coveted Casa Marina neighborhood. Completed in 2017, the home blends architectural elegance with comfortable everyday living, surrounded by lush landscaping and lighting throughout. At the heart of the home, a grand living room features soaring ceilings, cove lighting, and expansive NanaWall impact glass doors that open on both sides to both the pool and backyard patio. Designed for entertaining, the outdoor space features a substantial dining area and built-in kitchen. Inside, the kitchen and dining room are thoughtfully separated from the living room by a wall, with two connecting passages providing an easy flow between the spaces. The chef's kitchen showcases semi-precious dumortierite quartz countertops and premium Thermador appliances. A striking powder room features crushed Capiz shell wallpaper, an illuminated onyx sink, and a bronze waterfall faucet. The first-floor primary suite opens to an orchid potting garden on one side and an oversized outdoor shower on the other. Its bath features a private water closet and a six-foot window welcoming natural light. Upstairs, a bedroom or office offers a private terrace overlooking the pools, while two additional ensuite bedrooms share a den complete with a wet bar, and a full-size laundry room From the coral stone entry pathways over interconnected pools to the glass-railed staircase, and espresso Acacia wood flooring, thoughtful details distinguish this home. Additional amenities include a covered carport with a motorized door and EV charging, a whole-house generator, and a heated and chilled pool.

1119 Johnson St, 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
3821 Eagle Ave, Key West
$2,199,000
3 Beds ⋅ 2 Baths ⋅ 621869 MLS
Beyond the doors of 3821 Eagle Avenue, a private courtyard evokes the intimacy of a Tuscan retreat. Cascading vines, sculptural bougainvillea and lush greenery frame the 29x15 pool while a shaded terrace invites long lunches that linger into evening. Expansive folding glass doors connect the interiors to the outdoors allowing gatherings to flow naturally from kitchen to poolside. Warm wood cabinetry and a substantial waterfall edge island anchor a kitchen that knows culinary appointed with a Wolf induction range, Wolf hibachi grill, Double Fulgor Milano ovens and Hestan wine refrigeration. Generous surfaces invite abundant platters and conversation while the outdoor kitchen complete with a sink, two gas burners and a large Green Egg extends the experience into the garden. Large impact windows bring garden views into the bedrooms and living spaces keeping the surrounding greenery in sight throughout the home. The home balances open spaces for entertaining with the privacy of a personal escape. Its setting on Eagle Avenue, a beautiful wide street with sidewalks seldom found in Key West, completes a home with a distinctly Mediterranean sensibility and an unmistakable island soul.

3821 Eagle Ave, Key West
1104 Packer St, Key West
$2,249,000
4 Beds ⋅ 4 Baths ⋅ 621864 MLS
Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

1104 Packer St, Key West
1709 Catherine St, Key West
$979,000
3 Beds ⋅ 2 Baths ⋅ 621825 MLS
Available for immediate occupancy and offered at $979,000, 1709 Catherine Street combines a modern open floor plan with a spacious lot. This 3 bedroom and 2 bath home sits on more than 6,800 sq. ft., offering ample outdoor space and potential for future expansion. The fully fenced rear yard features a patio, a generous, covered porch, and a versatile 14 x 10 storage shed. With its substantial size, open space free of protected trees, and access for equipment, the yard offers potential for a swimming pool addition. A wide gate on the right side provides access for boat, RV, or additional vehicle parking, as permitted by code. Off-street parking accommodates 3 or more cars, with potential to add an EV charging station. A newer metal roof and impeccably maintained exterior complement the home's practical features, including wiring, plumbing, and propane tanks in place for the addition of a whole-house generator. Enjoy all the conveniences of living on the preferred western half of the island. Photos were taken in 2025 and are considered a fair representation of the property.

1709 Catherine St, Key West
1125 Angela St, Key West
$2,099,000
5 Beds ⋅ 4 Baths ⋅ 621819 MLS
Rare old town 4 unit property. On the corner of Angela and Ashe streets. This property consists of a 2 bedroom unit and 3 1 bedroom units. All units have separate water and electric meters. Each unit has dedicated outdoor space. This is a perfect investment property. Buyers would need to verify use and refurbishment with the City. Currently two units have long term tenants. Two units are vacant. This is a great opportunity in a perfect location.

1125 Angela St, Key West
1519 Johnson St, Key West
$2,190,000
5 Beds ⋅ 4 Baths ⋅ 621798 MLS
Discover island living at this spacious two-story, 5-bedroom, 4-bathroom retreat nestled in a quiet residential neighborhood right in the heart of Key West. Perfectly positioned this inviting property offers easy access to the beaches, tennis and pickleball courts, bocce courts, and the local dog park. Enjoy a leisurely bike ride to the vibrant energy of downtown Key West and Duval Street, then return home to your own private tropical escape. Inside, an open and welcoming floor plan features beautiful gray-blue tile flooring, a stylish kitchen, and generous living and dining areas designed for gathering with family and friends. With room to accommodate up to 14 people, the home offers exceptional flexibility for a large family, visiting guests, or those seeking a second home with income potential. The upper level provides two additional rooms, ideal for extra sleeping space, a home office, or a relaxing den. Step outside to a private backyard oasis featuring lush tropical landscaping, an expansive swimming pool, and a spacious deck perfect for outdoor dining, entertaining, and soaking up the Florida sunshine. A detached pool house adds another dimension of versatility, complete with a one-bedroom, one-bathroom studio and kitchenette--ideal for guests or additional living space. Offered fully furnished and with a history of vacation rental income, this property presents an exciting opportunity for investors seeking an income-producing asset or buyers looking to combine a personal island getaway with rental potential. Whether you envision a welcoming family retreat, a second home in paradise, or an investment in the Florida Keys lifestyle, 1519 Johnson Street offers space, flexibility, and a desirable central location to make it your own.

1519 Johnson St, Key West
2601 S Roosevelt Blvd Unit 610A, Key West
$995,000
3 Beds ⋅ 2 Baths ⋅ 621777 MLS
This stunning 3 bedroom penthouse condo overlooks the ocean, pool, and has a bird's eye view of the Gulf. Brilliant white, crisp kitchen with updated appliances and smartly appointed living/dining room, this is a home ready for living the Key West Beach Life! Updated bathrooms feature one with a tub, and one with a large walk-in shower. Bright cheery bedrooms and an in-condo laundry round out this PERFECT oceanview piece of Paradise!

2601 S Roosevelt Blvd Unit 610A, Key West
115 Front St Unit APT 101, Key West
$2,250,000
3 Beds ⋅ 3 Baths ⋅ 621771 MLS
Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

115 Front St Unit APT 101, Key West
817 Pearl St, Key West
$825,000
1 Beds ⋅ 1 Baths ⋅ 621769 MLS
Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by! Home Owners insurance is $ 1471.58, Flood Insurance is $ 1463.00

817 Pearl St, Key West
2827 Harris Ave, Key West
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 621768 MLS
This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West
711 Olivia St, Key West
$2,895,000
3 Beds ⋅ 3 Baths ⋅ 621758 MLS
Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X flood zone and offered turnkey. Some historic homes ask their next owners to take on a century of hidden repairs. This one asks only that you move in. With great care and pride, the owner restored the house from foundation to roof: a new foundation, new windows and siding, all-new electrical and plumbing, and every system beneath the surface brought current. The result is the character of an Old Town classic with the soundness of a home built today, and none of the worries that usually come with an older house. Inside, the main house is arranged as a 2BD/2BA, with both bedrooms ensuite, giving each occupant a private retreat of their own. Outside, the pool sets the tone for long winter afternoons in the tropical sun. Beside it, a separate 1BD/1BA guest cottage gives visiting family or friends their own quarters and bath, so everyone can share the season while keeping their privacy. Off-street parking for one car, a true premium in Old Town, makes arrivals and departures easy. The home is offered fully turnkey, with interiors curated by local designer Amie Woeppel, so a seasonal owner can arrive, unpack, and start living, with nothing left to fix or furnish. Every choice reflects an owner who restored this house to be lived in and loved, not simply sold. From the front door, Duval Street is a six-minute walk, with a wide selection of restaurants and bars along the way. Old Town history, rebuilt from the ground up and ready for its next chapter.

711 Olivia St, Key West
Start Your Search

How much is your home worth?

Get instant property value now!