Vacation Rentals by Owner

Poolside Paradise is a cozy, 1930s-era pool cottage lovingly renovated into a 1B/1BA suite. The sage-green exterior blends Caribbean, Victorian, and contemporary influences: crisp white trim and sky-blue Bermuda shutters.

This intimate, poolside cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated courtyard community of five historic Old Key West vacation rentals. The spacious pea-gravel courtyards boast tropical landscaping, coral and rock hardscaping, and 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, gated enclave of six historic Old Key West vacation rentals. There’s also a shared laundry area with commercial washers & dryers.

Poolside Paradise was once the guest suite/pool cottage of Toon Hall. Toon Hall was owned (and aptly named) by 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, Poolside Paradise offers a cozy island suite beside the pool and courtyard in a gated enclave of elegant vacation properties.
Sip Cafe Cubano at the covered, alfresco dining table as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita. Prepare a light tropical meal in the kitchenette. 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.
Street parking is available out front. Poolside Paradise has one King Bed, ideal for couples or solo travelers. The home has an all-new water filtration system.
Are you 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:
Poolside Paradise is a bright, airy, one-room living space with tile floors, large windows, raised ceilings, exposed beams, a ceiling fan, and an interior color palette of crisp white and earthy neutrals. A built-in desk/TV stand boasts a Smart TV with Roku. Stream your favorite shows or movies. French doors open to a covered alfresco dining area with rattan benches. Enjoy easy-breezy indoor/outdoor living space.
Kitchen/Dining:
The sunny kitchenette has tile floors, abundant cabinets, and Formica countertops. Appliances include a compact fridge, microwave, farmhouse-style sink, coffee maker, and toaster. Prepare sandwiches or a light island-style meal after a day at the beach! The kitchenette has a dinette with seating for two. French doors from the kitchen lead directly to covered alfresco dining and to the pool deck, making for seamless indoor/outdoor entertaining.

Bedrooms/Baths:
Poolside Paradise has one air-conditioned bedroom and one bathroom. There is one King bed. Matching rattan-style bedside tables have reading lamps. A built-in TV stand/desk boasts a Smart TV.

The sparkling-clean, remodeled bathroom has a single-sink vanity, a walk-in glass door shower, a water-saving toilet, toiletries, and a hair dryer.

Bedroom Overview:
Primary: King Bed, Ensuite bath w/ walk-in 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 patio. This dining space seats two. The whitewashed fence buffers 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, gated enclave of six historic, Old Key West vacation rentals.) 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.

If you’ve been charmed by the magic of Toon Hall and wish to learn more about the life and work of Jeff MacNelly, tour the island art galleries and pay a visit to Gallery on the Greene, the exclusive gallery representing MacNelly. While cartooning was MacNelly’s livelihood, he was skilled in many media, including oil, acrylic, and clay (sculpture). Today, The Community Foundation of the Florida Keys honors the legacy of Jeff MacNelly with a youth scholarship, The Jeff MacNelly Memorial Scholarship Award, which helps students in Monroe County to further their art careers.