Tropical Village: Poolside Paradise by RENT KEY WEST VACATIONS

Key West, Florida
$291 avg/night
Bed 1

Bed

Bath 1

Bath

Home Apartment

Property Type

Sleep 2

Max Sleeps

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    Bed Sheets Provided
  • GENERAL

    Unit Size: 329 Sq Ft (31 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Microwave Refrigerator Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required
  • INTERNET

    Internet Access
  • OUTDOORS

    Garden Gas Grill
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    1 Bathroom Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Fitness Facilities Nearby Kayaking Nearby Marina Nearby Parasailing Nearby Power Boating Nearby Snorkeling Nearby Swimming Nearby Water Tubing Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Tile Flooring In Public Areas

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Rates & Availability

Review Review

  • Michael C.

    Submitted Oct 31, 2025

    Stayed Oct 20, 2025

    It was so fun! Thanks so much!!

  • Karen R.

    Submitted Jun 7, 2025

    Stayed May 31, 2025

    We loved the location of the property and enjoyed our stay.

  • Gregory L W.

    Submitted Jun 6, 2025

    Stayed May 25, 2025

    Quiet, nice location. Well equipped and steps from the wonderful pool. Great couples getaway stay.

  • Karen F.

    Submitted May 9, 2025

    Stayed May 2, 2025

    The pool was beautiful, very clean, as was the property. We weren’t aware that there was no convenient parking, but overall it was nice place.

  • Mary L.

    Submitted Apr 15, 2025

    Stayed Apr 4, 2025

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

  • Julie L.

    Submitted Apr 14, 2025

    Stayed Mar 26, 2025

    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).

  • Morris M.

    Submitted Mar 22, 2025

    Stayed Mar 15, 2025

    Exceeded expectations-best kept secret in Key West!

  • Charles K.

    Submitted Mar 12, 2025

    Stayed Mar 2, 2025

    Off the beaten path, walking distance to everything.

  • Karen G.

    Submitted Feb 26, 2025

    Stayed Feb 13, 2025

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

  • Kathy E.

    Submitted Feb 9, 2025

    Stayed Jan 29, 2025

    Our stay was ok. There were several things that did not work the first few days...toilet, outside lights. And, we needed to unplug the refrigerator to use the microwave. These were repaired quickly but still. Things that could have enhanced the stay were, beach chairs so we did not have to rent, info in the room about how to get around, etc. The heated pool was very nice and we were in several times. It was a four block walk to the free bus; three blocks to get coffee or a meal and the so called grocery was poorly stocked. In short it was an ok place but the location was not really convenient for much.

  • Laurie C.

    Submitted Jan 26, 2025

    Stayed Jan 4, 2025

    There was nothing redeeming about our accommodations. Very disappointed!

  • Jodi M.

    Submitted Dec 5, 2024

    Stayed Nov 26, 2024

    Perfect location close to Southernmost point and a local grocery store which was very convenient. The pool was clean and warm and the laundry facilities were a nice bonus. The unit had everything we needed for our stay. The only thing I would add is a fan for noise as the Roosters crow at all hours and that would have helped drown them out. Otherwise it was a fabulous place to stay for two and we would stay again.

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Total

Includes taxes and fees
$291+
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