Poolside Paradise @ Tropical Village

0 Bedrooms 1 Bathrooms Sleeps 2 Key West 329 sq. ft. Pet Friendly

Cozy 1/1 poolside Conch cottage has a storied past as the winter retreat of Pulitzer cartoonist Jeff MacNelly, illustrator of the comic strip Shoe. Kitchenette/dinette. Common area (pool/deck/laundry) shared by gated enclave of 6 historic rentals.

Poolside Paradise is a cozy, 1930s-era pool cottage lovingly renovated into a studio 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.

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

Accommodation Essentials

  • Hangers
  • Kitchen
  • Wireless Internet
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Dryer
  • Iron & Ironing Board
  • Shampoo
  • Washer
  • Body Wash

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

Kitchen

  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Dining table
  • Blender

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Outdoor

  • BBQ Area
  • Patio or Balcony
  • Grill

Car

  • Not Necessary

Entertainment

  • Satellite or Cable
  • Television
  • Smart TV

Facility

  • Pool
  • Single Level Home
  • Street Parking

Location

  • Historic District
  • Near Ocean
  • Casa Marina

Pool

  • Communal Pool
  • Heated Pool
LEAVE A REVIEW
April 14, 2025 - VRBO

A lovely time

by Julie Q

Our booking experience with RENT KEY WEST VACATIONS was seamless. Real people answering calls in real time, very friendly and reponsive. Poolside Paradise was in a GREAT location a block or two from clean and not to crowded beaches, a couple blocks from a FABULOUS cuban coffee place and market, and an easy walk to excellent restaurants. The accommodations were very cozy - basically a one room studio with bathroom. The pictures are very accurate. The connection to the cartoonist Jeff McNally added charm. One of two of the owners were onsite which made for good conversation, local tips on restaurants, and a greater sense of comfort and safety.A few suggestions: The description said the pool was heated. It is not, so dips were VERY refreshing. The safe in the room was broken and non-operational. The rug in the room should be replaced and we dealt with it by rolling it up and tucking it under the bed for the duration of our stay. Overall, the room could use some remodeling / upgrades in spots that are a bit too worn. We heard that there has been a recent change in management companies so perhaps these bits are already on the punch list! Overall, a lovely stay. It was our first time in Key West. We definitely did not need a car, had planned to rent bikes but ended up just walking everywhere (4-10 miles a day!). Our favorite restaurants included Blue Heaven, Santiago's Bodega, and Grignote (all phenomenal, friendly and also very safe for folks requiring gluten free fare).

Julie, 

 

Thank you SO much for the kind words! We truly enjoyed having you as our guest and look forward to your return. Thank you also for the suggestions of improvements. You will be happy to know we have ordered the rug and safe to be replaced! 

April 13, 2025 - Track Survey

by Mary L

A nice, quiet, safe location, although construction going on at house behind us. Pool and grounds were lovely. We walked to beaches and Duval St.

Thank you for your review Mary. We are happy to see you were able to enjoy your stay despite the ongoing construction that is happening in the surrounding areas. 

March 30, 2025 - Airbnb

by Thomas & Theresa

Great location. Pool very cold Easy check in and any questions were answered promptly! Thanks for a great stay!!

March 26, 2025 - Track Survey

by Morris M

Old Town charm-very quiet and private. Great location-very convenient to Duval St action!

February 26, 2025 - VRBO

Loved the place

by Karen G

Loved that we walked out from our private patio to a lovely pool. Enjoyed visiting with our neighbors. The place had everything we needed.

February 14, 2025 - Track Survey

by Tom L

I loved everything about it! Was just the perfect stay for me, and I hope to return next season or perhaps for a day or two in the spring!

January 29, 2025 - Airbnb

by Michelle

Our stay in Poolside paradise was just that! Hosts were quick to respond to our questions. Pool area nice, warm and clean. I would return again in a heartbeat!

October 31, 2024 - Track Survey

by Michael S

Perfect space and location for our needs. Will definitely be returning.

Thank you Michael! We look forward to your return!!

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May 2025
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August 2025
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September 2025
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October 2025
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November 2025
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December 2025
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$559
     
January 2026
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February 2026
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April 2026
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$394
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$382
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$380
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$386
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May 2026
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$285
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$272
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$269
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$277
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$245
           

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