Toon Hall @ Tropical Village

3 Bedrooms 2 Bathrooms Sleeps 10 Key West 1400 sq. ft. Pet Friendly

Spacious 3BR/2BA 1930s-era Conch cottage w/ a storied past! Toon Hall was the winter retreat of Pulitzer Prize cartoonist Jeff MacNelly, illustrator of the comic strip Shoe. Private decks w/ alfresco dining. The common area (pool, deck w/ grill, picnic ta

Primary Bedroom

1 King

Second Bedroom

1 King

Third Bedroom

1 Queen

Living Room- Sofa Bed

2 Sofa Bed

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 six 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 6-plex. There’s also a shared laundry area with commercial washers & dryers.
Toon Hall was aptly named by its owner, Jeff MacNelly (1947-2000), lauded as one of the most brilliant political cartoonists of all time. 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. MacNelly cherished the vibrant Key West arts scene as his wintertime retreat.
Sip Cafe Cubano on the private back deck as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita in hand. Jeff MacNelly, the celebrated political cartoonist, would surely be pleased to see guests enjoying his beloved island paradise. He would be poking fun at everyone, making witty remarks, and reminding guests to stay humble, embrace their goofy side, and not take life too seriously.

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. 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. Jeff MacNelly’s cartoons, pen and ink drawings, and original canvases are on display at the Gallery on Greene.

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.

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.

Just off the kitchen, 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 Double 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 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.

Kitchen

  • Coffee Maker - Drip
  • Cooking Basics
  • Oven
  • Stove
  • Blender
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Dishwasher
  • Room
  • Dining table

Accommodation Essentials

  • Dryer
  • Iron & Ironing Board
  • Shampoo
  • Washer
  • Body Wash
  • Hangers
  • Kitchen
  • Wireless Internet
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Essentials
  • Living Room
  • Private Entrance
  • Private Living Room
  • Desk
  • Office
  • Desk

Facility

  • Street Parking
  • Pool
  • Single Level Home

Entertainment

  • Television
  • Satellite or Cable
  • Smart TV

Pool

  • Communal Pool
  • Heated Pool

Tourist Attractions

  • Health Beauty Spa
  • Marinas, Boat Rentals & Excursions
  • Museums
  • Key West Aquarium
  • Public Parks & Beaches
  • Key West Historic Seaport
  • Key West Tropical Forest & Tropical Garden
  • Southernmost Point Buoy
  • Dry Tortugas National Park & Fort Jefferson
  • Fort Zachary Taylor State Park & Beach
  • Sunset Celebration at Mallory Square
  • History Tours - Motorized, Walking & Biking
  • The Florida Reef - N. America’s only living coral barrier reef
  • Key West Marine Park stretching from Higgs Beach to South Beach
  • The Key West Butterfly & Nature Conservatory
  • Food Tours
  • Ghost Tours
  • Pub Crawls
  • Your reservation guest portal will provide details

Sports

  • Paddle Boarding
  • Fishing - Surf
  • Hiking
  • Banana Boat Riding & Water Tubing
  • Wind Surfing
  • Ocean Waterpark & Challenge Course
  • Kayaking
  • Kite Boarding
  • Pickleball
  • Tennis
  • Golfing
  • Scuba Diving
  • Skydiving
  • Your reservation guest portal will provide details
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming

Leisure

  • Dolphin Watching
  • Dining Out
  • Live Theater, Concerts & Entertainment
  • Your reservation guest portal will provide details
  • Paint & Sip Art Classes
  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Local

  • Banks
  • Grocery Stores
  • Fitness Centers
  • Hospital
  • Laundromats

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Outdoor

  • BBQ Area
  • Garden or Backyard
  • Patio or Balcony
  • Deck Patio Uncovered
  • Grill

Car

  • Not Necessary

Location

  • Historic District
  • Near Ocean
  • Casa Marina

Themes

  • Family
  • Historic
LEAVE A REVIEW
July 13, 2025 - Track Survey

by Joshua J

The rental property was beautiful, and the shared pool was amazing. We met some new friends, and the location was absolutely fantastic. 

March 11, 2025 - VRBO

by Shelley W

I wish I could have stayed longer at Toon Hall. It has a lot of room for everyone to spread out and relax. I love the french doors out 2 of the bedrooms to the back patio and then to the pool. Everyone was friendly and check in/out was easy from the app

February 20, 2025 - Track Survey

by Shelley W

We loved Toon Hall and had a great experience with Rent Key West Vacations! Thank you!

You are so very welcome and we hope to have you return again soon!!

January 22, 2025 - VRBO

Long weekend in Key West

by Christopher L

The home was very clean and well appointed. Good location. Overall an excellent experience

December 30, 2024 - VRBO

Christmas Presence

by Stacy L

We thoroughly enjoyed this beautiful home. Spending Christmas in Key West is a very relaxing way to enjoy being with family. The location is perfect: close to all the things we love!

Thank you for your kind review! We're so happy to hear that you had a relaxing Christmas with your family in Key West and that the home and location were perfect for your stay. We'd love to welcome you back for more memorable vacations in the future!

December 1, 2024 - Airbnb

by Kelly H

Great house, plenty of space, better than the pictures and description. Host was very responsive and we even extended our stay.

July 8, 2024 - Airbnb

by Stephanie A

Toonhall did not disappoint! We visited this house for Fourth of July weekend with our employees and kids, and everyone really enjoyed themselves. We were even able to see fireworks from the front porch. The cartoon pictures on all the walls were quite entertaining. The pool was very clean and the atmosphere setting and neighborhood was peaceful yet busy as to be expected. Literally one street away from Duval was perfect. We would definitely visit this house again.

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September 2025
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October 2025
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$723
 
November 2025
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$658
           
December 2025
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January 2026
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February 2026
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March 2026
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$956
       
April 2026
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$968
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May 2026
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$815
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$787
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$807
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$781
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$761
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$743
           
June 2026
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$743
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$739
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$764
       
July 2026
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$752
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$795
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$821
 
August 2026
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$803
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$571
         
September 2026
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$563
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$556
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$551
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$594
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$556
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$544
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$536
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$529
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$511
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$531
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$512
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$494
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$527
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$511
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$498
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$503
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$505
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$509
     

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