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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September 2026
S M T W T F S
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$468
05
06 07
$350
08
$350
09
$350
10
$350
11
$388
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13
$350
14
$350
15 16 17 18
$405
19
$431
20
$363
21
$350
22
$356
23
$354
24
$401
25
$441
26
$499
27 28 29 30      
October 2026
S M T W T F S
        01 02 03
$551
04
$485
05
$482
06
$480
07
$459
08 09 10
11
$680
12
$664
13
$662
14
$606
15
$703
16
$783
17
$894
18
$885
19
$823
20 21 22 23 24
25 26
$700
27
$670
28
$668
29
$738
30
$769
31
$793
November 2026
S M T W T F S
01
$715
02
$697
03
$745
04
$895
05
$944
06 07
08 09
$791
10
$864
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$852
12
$935
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$941
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$913
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$746
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$706
17
$682
18
$589
19 20 21
22 23
$734
24
$728
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$706
26 27 28
29 30
$459
         
December 2026
S M T W T F S
    01
$466
02
$571
03 04 05
06
$658
07
$615
08
$600
09
$616
10
$683
11
$709
12
$701
13
$605
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$576
15
$566
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$586
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$661
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$837
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$860
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$773
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$749
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$831
23 24 25 26
$1310
27
$1212
28 29 30 31    
January 2027
S M T W T F S
          01 02
$1323
03
$1123
04
$1018
05
$1020
06
$1048
07
$1148
08
$1161
09
$1033
10
$913
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$875
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$869
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$901
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$982
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$1059
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$1178
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$1088
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$968
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$989
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$980
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$1094
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$1088
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$1080
24
$1035
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$963
26
$1107
27 28 29 30
31
$1075
           
February 2027
S M T W T F S
  01
$1025
02
$957
03
$992
04
$1123
05
$1240
06
$1257
07
$1134
08
$1070
09
$1057
10
$1091
11
$1219
12
$1325
13
$1402
14
$1270
15
$1275
16
$1281
17
$1222
18
$1373
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$1413
20
$1424
21
$1237
22
$1159
23
$1160
24
$1190
25
$1320
26
$1368
27
$1346
28
$1197
           
March 2027
S M T W T F S
  01 02 03 04 05 06
$1375
07
$1233
08
$1202
09
$1210
10
$1205
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$1311
12
$1348
13
$1367
14
$1247
15
$1246
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$1327
17
$1238
18
$1313
19
$1346
20
$1288
21
$1153
22
$1038
23
$1030
24
$1132
25
$1237
26
$1213
27
$1207
28
$1065
29
$1045
30
$958
31
$1103
     
April 2027
S M T W T F S
        01
$1187
02
$1110
03
$1102
04
$947
05
$888
06
$1035
07
$1054
08
$1152
09
$1022
10
$1015
11
$888
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$843
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$839
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$869
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$948
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$984
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$989
18
$862
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$818
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$806
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$825
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$909
23
$949
24
$959
25
$853
26
$810
27
$803
28
$885
29
$978
30
$1022
 
May 2027
S M T W T F S
            01
$1012
02
$887
03
$746
04
$730
05
$732
06
$804
07
$851
08
$841
09
$734
10
$691
11
$689
12
$700
13
$775
14
$812
15
$822
16
$725
17 18 19 20 21 22
$813
23
$823
24
$767
25
$760
26
$749
27
$848
28
$935
29
$942
30
$728
31
$719
         
June 2027
S M T W T F S
    01
$853
02
$829
03
$876
04
$875
05
$879
06
$780
07
$737
08
$731
09
$750
10
$824
11
$876
12
$905
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$736
14
$683
15
$738
16
$756
17
$844
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$902
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$929
20
$822
21
$750
22
$726
23
$752
24
$839
25
$878
26
$886
27
$805
28
$744
29
$738
30
$772
     
July 2027
S M T W T F S
        01
$773
02
$782
03
$819
04
$776
05
$672
06
$662
07
$673
08
$769
09
$815
10
$827
11
$658
12
$603
13
$603
14
$619
15
$683
16
$732
17
$757
18
$672
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$623
20
$611
21
$630
22
$710
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$794
24
$861
25
$740
26
$778
27
$733
28
$696
29
$788
30
$810
31
$735
August 2027
S M T W T F S
01
$637
02
$577
03
$580
04
$581
05
$648
06
$688
07
$706
08
$596
09
$523
10
$521
11
$532
12
$591
13
$629
14
$639
15
$543
16
$478
17
$464
18
$476
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$541
20
$579
21
$588
22
$500
23
$433
24
$420
25
$446
26
$522
27
$556
28
$579
29
$484
30
$430
31
$426
       
September 2027
S M T W T F S
      01
$393
02
$497
03
$496
04
$555
05
$512
06
$508
07
$487
08
$388
09
$441
10
$503
11
$505
12
$410
13
$359
14
$375
15
$383
16
$446
17
$522
18
$493
19
$396
20
$350
21
$370
22
$383
23
$439
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$498
25
$485
26
$410
27
$381
28
$367
29
$375
30
$468
   

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