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 and 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 and 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
  • Hair Dryer
  • 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
August 11, 2026 - Track Survey

by Manuel C

It had everything we needed for our trip! Would rent again

Thank you for your wonderful review! We're so glad the home had everything you needed for your trip. We look forward to welcoming you back again soon!

May 21, 2026 - Track Survey

by Jamin R

We had a wonderful time! We were glad to have plenty of bath towels as well as pool towels to use.

Thank you for your wonderful review! We're so glad you had a great stay and that the ample supply of bath and pool towels helped make your visit more comfortable and convenient.

We appreciate you choosing to stay with us and hope to welcome you back again soon!

February 26, 2026 - Track Survey

by Lisa A

We had everything we needed and the location was perfect!

February 10, 2026 - Airbnb

by Tera B
Enjoyed our stay! Great location, quiet neighborhood, easy to make your way to do all the things in Key West - by foot, bike, cart, or car ride. The space was nice, beds were comfortable, lots of room to lounge outside by the pool or three other large, private-feeling porches. Only heads up, the leaf blower guy comes every morning around 9:00am to respectfully clean around the pool areas, but the rooster(s) crows earlier 😉 Great experience overall!
 
February 8, 2026 - Airbnb

by Brian B

 

Great location and spacious accommodations
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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October 2026
S M T W T F S
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04 05 06 07 08 09 10
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18 19 20 21 22
$800
23 24
25 26
$350
27
$350
28
$350
29
$364
30
$436
31
$446
November 2026
S M T W T F S
01
$462
02
$424
03
$451
04
$473
05
$812
06 07
08 09
$475
10
$473
11
$509
12
$513
13 14
15 16 17
$360
18
$553
19 20 21
22 23
$490
24
$496
25
$741
26 27 28
29 30
$398
         
December 2026
S M T W T F S
    01
$409
02
$564
03 04 05
06
$522
07
$496
08
$476
09
$487
10
$544
11
$593
12
$617
13
$540
14
$505
15
$500
16
$522
17
$634
18
$685
19
$739
20
$616
21
$653
22
$667
23 24 25 26
27 28 29 30 31    
January 2027
S M T W T F S
          01 02
$1232
03
$1026
04
$929
05
$900
06
$920
07
$1002
08
$1038
09
$1031
10
$932
11
$886
12
$881
13
$909
14
$1012
15
$1190
16
$1271
17
$1161
18
$1000
19
$1014
20
$957
21
$1074
22
$1106
23
$1108
24
$998
25
$928
26
$1061
27 28 29 30
31
$1018
           
February 2027
S M T W T F S
  01
$967
02
$968
03
$1016
04
$1140
05
$1236
06
$1266
07
$1119
08
$1079
09
$1074
10
$1104
11
$1215
12
$1329
13
$1430
14
$1313
15
$1281
16
$1287
17
$1251
18
$1389
19
$1436
20
$1408
21
$1247
22
$1172
23
$1156
24
$1203
25
$1336
26
$1379
27
$1336
28
$1189
           
March 2027
S M T W T F S
  01 02 03 04 05 06
$1311
07
$1209
08
$1217
09
$1212
10
$1218
11
$1283
12
$1382
13
$1417
14
$1277
15
$1351
16
$1460
17
$1350
18
$1348
19
$1304
20
$1303
21 22 23 24 25 26 27
$1228
28
$1094
29
$1075
30
$980
31
$997
     
April 2027
S M T W T F S
        01
$1073
02
$1130
03
$1120
04
$977
05
$970
06
$892
07
$906
08
$1001
09
$1038
10
$1032
11
$909
12
$864
13
$862
14
$875
15
$998
16
$1060
17
$1054
18
$885
19
$837
20
$827
21
$847
22
$928
23
$967
24
$972
25
$873
26
$812
27
$809
28
$893
29
$991
30
$1124
 
May 2027
S M T W T F S
            01
$1090
02
$811
03
$761
04
$738
05
$750
06
$822
07
$891
08
$894
09
$750
10
$707
11
$695
12
$720
13
$813
14
$838
15
$839
16
$782
17 18 19 20 21 22
$894
23
$905
24
$844
25
$822
26
$801
27
$933
28
$1029
29
$1036
30
$756
31
$747
         
June 2027
S M T W T F S
    01
$738
02
$668
03
$777
04
$963
05
$967
06
$730
07
$697
08
$628
09
$649
10
$717
11
$762
12
$996
13
$810
14
$751
15
$708
16
$664
17
$736
18
$773
19
$774
20
$682
21
$641
22
$638
23
$654
24
$723
25
$780
26
$761
27
$695
28
$648
29
$646
30
$673
     
July 2027
S M T W T F S
        01
$791
02
$797
03
$836
04
$800
05
$698
06
$689
07
$698
08
$767
09
$785
10
$765
11
$685
12
$637
13
$636
14
$657
15
$775
16
$824
17
$826
18
$702
19
$657
20
$650
21
$670
22
$750
23
$798
24
$877
25
$775
26
$788
27
$811
28
$800
29
$835
30
$836
31
$761
August 2027
S M T W T F S
01
$668
02
$614
03
$603
04
$609
05
$678
06
$720
07
$721
08
$621
09
$560
10
$540
11
$670
12
$612
13
$655
14
$644
15
$546
16
$490
17
$475
18
$491
19
$557
20
$595
21
$600
22
$505
23
$444
24
$431
25
$448
26
$534
27
$583
28
$616
29
$513
30
$463
31
$467
       
September 2027
S M T W T F S
      01
$426
02
$545
03
$622
04
$645
05
$584
06
$578
07
$502
08
$407
09
$466
10
$487
11
$477
12
$410
13
$364
14
$355
15
$370
16
$428
17
$469
18
$473
19
$413
20
$370
21
$366
22
$386
23
$459
24
$482
25
$494
26
$430
27
$376
28
$379
29
$397
30
$460
   
October 2027
S M T W T F S
          01
$511
02
$523
03
$481
04
$430
05
$424
06
$450
07
$505
08
$570
09
$595
10
$530
11
$532
12
$543
13
$486
14
$557
15
$611
16
$627
17
$552
18
$812
19
$872
20
$943
21
$1098
22
$1235
23
$1135
24
$807
25
$733
26
$717
27
$693
28
$709
29
$753
30
$754
31
$642
           

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