Fall family fun in Key West: The best island delights for kids this season
After the summer crush, many vacation destinations wind down in the fall, but Key West comes alive — with sunny skies, ocean breezes, and the perfect blend of relaxation and adventure for families.
Planning a trip between September and November? Fall is one of the best times to explore the island with kids. You’ll find far fewer tourists and milder temperatures, making family activities much more accessible, and enjoyable.
The perfect time for a Key West family getaway
Key West’s shoulder season offers the best of both worlds: ideal weather (mid-70s to low 80s), fewer tourists, and great rates on accommodations. You’ll enjoy warm beach days and stunning sunsets, minus the hustle and noise of peak season. And when you stay in a beautifully appointed home from Historic Key West Vacation Rentals, you can keep the fun going from morning splash time to starlit swims.
Here are some of our favorite suggestions for the ultimate family getaway in in Key West this fall.
Top family-friendly things to do in Key West (fall edition)
1. Visit the Key West Aquarium
Little ones will be fascinated watching a shark feeding, touching sea cucumbers and sea stars, and exploring all the amazing marine life native to the Keys. You’ll find The Key West Aquarium is a compact, hands-on experience created with young kids in mind. Add to this, all the special features and activities designed to celebrate the institution’s 90th birthday, and you’ve planned the perfect day.
2. Climb the Key West Lighthouse
Older kids and teens will enjoy the adventure of climbing 88 steps to the top of the historic Key West Lighthouse, which lit the way for military and commercial vessels as they navigated the reefs surrounding the Keys. You’ll be rewarded with jawdropping panoramic views of the island — and take in some cool history along the way via exhibits at the Keeper’s Quarters Museum.
3. Get spooked (in a good way) on a ghost tour
October brings out all the famous ghosts of Key West! Try a family-friendly walking tour or hop aboard the Ghosts & Gravestones trolley. It’s a fun (and not-too-scary-for-kids) way to hear about the island’s haunted past.
4. Explore Fort Zachary Taylor Historic State Park
Spend a day with the family at Fort Zachary Taylor State Park, and experience Key West’s most fabulous beach. Pack a picnic, snorkel among the corals and tropical fish, try your hand at fishing, bird watching and walking beautiful nature trails. Beach and water-sport equipment are available for rent, and the Civil War era fort is fascinating for budding historians.
5. Ride the Conch Tour Train
All aboard the Conch Tour Train! This festive narrated tour of the city is as entertaining as it is informative — and lets kids cool off and rest their feet while taking in the sights. You’ll hear all kinds of stories of Key West, and get up-close glimpses of all the city’s highlights and attractions.
6. Visit the Turtle Hospital or Dolphin Research Center
If you’re up for a short drive to Marathon (about an hour outside of town), these two attractions are unforgettable. The Turtle Hospital is a nonprofit conservation organization dedicated to researching, tracking, and rehabilitating endangered sea turtles. You can join a guided 90-minute tour of the facility and learn all about the care and feeding of the institution’s sea turtles. At the Dolphin Research Center, you’ll learn all about these special mammals and even interact with them in an outdoor lagoon.
7. Fall festivals and events
Join in some of our special fall events, where there’s something for every family member to enjoy. The Goombay Festival (Oct. 17-18) celebrates Caribbean culture with food, dancing, arts and crafts, and family-friendly activities in Key West’s historic Bahama Village neighborhood, The Key West Film Festival (Nov. 12–16) celebrates an eclectic variety of films that honor the creative spirit of Florida-based filmmakers. Here, you can seek out some family-friendly screenings geared for adults and teen movie buffs.
Look to us for your family’s fall home base
Between outings, your Key West home-away-from-home should be just as fun and relaxing. That’s where Historic Key West Vacation Rentals comes in. Imagine mornings lounging on a breezy veranda, afternoons splashing in the pool with the kids, and evenings cooking dinner together in a fully equipped kitchen, then dining under the stars — no cramped hotel rooms or noisy lobbies in sight. Many of our historic homes also come with fenced yards, outdoor dining areas, and cozy spots for family game nights.
Our lovely vacation rental homes, condos, and cottages are situated in the most desirable areas of the island, many in Old Town, and feature charming architectural touches. You’ll be right in the middle of all the action and excitement, and our extensive portfolio of gorgeous family homes will capture your imagination. Contact our Guest Services team for help with your family vacation planning. We offer assistance arranging reservations, excursions, tours, fishing charters, transportation, and much more.
Here are just two of our family-favorite rentals:
- Sunny Daze Cottage: Here’s a charming 2BR, 2BA spacious retreat with a private heated pool, multiple bedrooms, and all the modern amenities families love. Sunny Daze Cottage is just a short walk from beaches, restaurants, and attractions, yet tranquil enough for mid-day naps and quiet mornings.
- Villa Azul: Gorgeous and private 3BR, 3BA Villa Azul sleeps six and offers a lush landscape out back. The spacious interior includes traditional Bahamian and British Colonial style furnishings. You’ll enjoy a beautiful private pool with a waterfall feature and a covered loggia for family meals out back, as well as an outdoor shower and pool house.
Published on Thursday, July 31, 2025