Toon Hall is a quintessential 1930s-era Conch home, lovingly renovated with contemporary island sophistication. A parquet brick walkway leads from the garden gate to the columned front entry of this iconic tropical retreat. The sage-green exterior blends Caribbean, Victorian, and contemporary influences: crisp white trim, detailed woodworking, and abundant windows.
This charming cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated complex of five historic Old Key West vacation rentals. The spacious pea-gravel courtyard boasts tropical landscaping, coral and rock hardscaping, and stone walkways leading to the shared pool area. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale 5-plex. There’s also a shared laundry area with commercial washers & dryers.
Toon Hall was aptly named by owner Jeff MacNelly (1947-2000), lauded as one of the most brilliant political cartoonists. In 1977, MacNelly launched his comic strip Shoe, characterized by wit, wry humor, and cynicism. He became The Chicago Tribune’s syndicated editorial cartoonist. Newsweek Magazine described MacNelly’s style as “goofy gracefulness.” In his lifetime, MacNelly received three Pulitzers and two Reuben Awards, the highest honor of the National Cartoonists Society. Since Jeff MacNelly’s death in 2000, the Shoe comic strip has been kept alive by Chris Cassatt, Gary Brookins, and Susie MacNelly.
Jeff MacNelly and his wife Susie cherished the vibrant Key West arts scene as a wintertime retreat. Today, Toon Hall offers a laid-back retreat where guests can embrace their goofy side, laugh amidst the company of friends and loved ones, and remember not to take life too seriously.
Sip Cafe Cubano on the private back deck as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita. Prepare a home-cooked meal in the modern kitchen. Dine alfresco when nights are fragrant with jasmine and frangipani. Stroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower.
After a day at the beach, shower off in the private, hot-water outdoor shower. Street parking is available out front. Toon Hall is ideal for families, groups of friends, couples, and snowbirds. The home has an all-new water filtration system.
Interested to learn more about the life and work of Jeff MacNelly? Pop into The Gallery on the Greene, the exclusive KW gallery representing MacNelly. Cartoons, pen and ink drawings, and original canvases are on display.

Living:
Bright, airy living spaces have tile floors, large windows, ceiling fans, and an interior color palette of earthy, neutral, and crisp white. Plush suede sofas, nicely arranged around distressed coffee tables, provide a relaxing space for conversation, socializing, or family gatherings. A built-in bookshelf boasts a Smart TV with Roku. Stream your favorite shows or movies. French doors open to a front deck with built-in benches. Enjoy easy-breezy indoor/outdoor living space.
A den offers a rattan-style computer desk and vintage rolling desk chair.
Kitchen/Dining:
The sunny kitchen has tile floors, large windows, hardwood cabinets, and granite countertops. Appliances include a glass-top electric stove, oven, microwave, dishwasher, full-size fridge, and farmhouse-style sink. Prepare a tropical feast after a day at the beach! A door from the kitchen leads directly to a side deck with alfresco dining, making for seamless indoor/outdoor entertaining.
The indoor dining room has tile floors, a ceiling fan, grand windows, and a solid yet rustic farmhouse-style dining table with seating for eight.

Bedrooms/Baths:
Toon Hall has three bedrooms and two bathrooms. There are two King beds, one Queen bed, and two double sofa beds. All three air-conditioned bedrooms have Smart TVs, tile floors, ceiling fans, closets, and rattan-style furniture (headboards, nightstands, bureaus & TV stands).
Both sparkling-clean, remodeled bathrooms have granite vanities, water-saving toilets, toiletries, and hair dryers. An outdoor shower offers rustic, tropical serenity, perfect for rinsing sand or chlorine after a day of island fun.
Bedroom Overview:
Primary: King Bed, Ensuite bath w/ walk-in shower
Bedroom #2: King Bed, access to hallway bath w/ tub/shower combo
Bedroom #3: Queen bed, access to hallway bath w/ tub/shower combo
Living Room: Two Twin Sofa Beds, access to private outdoor shower

Outdoor Amenities:
A tall exterior fence, lush gardens, and mature trees provide privacy, security, shade, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced side deck. This dining space seats six. The front deck, with built-in benches, is an idyllic spot for entertaining and socializing. A garden courtyard and whitewashed fencing buffer your private space from the central common area.
Cool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. This swimming pool will delight families, children, the very young, and the young at heart. (The common pool area is shared by guests of this upscale 5-plex.) The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.
Since laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers.
Discover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions.


The Neighborhood:

The proximity of Toon Hall to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience.

A car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away.
Stroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences.
Don't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Toon Hall, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public.
Higgs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach to Southern Cross. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities.
Approximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing.
Fort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset.
Seeking family-friendly activities or rainy-day excursions? Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.