Florida offers more than just standard hotel chains and beach resorts for families seeking memorable stays. From authentic treehouses nestled in forest canopies to historic lodges where presidents once slept, the Sunshine State provides accommodations that become part of the adventure itself. Here are fifteen extraordinary places where families can create lasting memories while experiencing Florida in ways that go far beyond the typical vacation rental.
Hawks Cay Resort
This family-friendly destination is located in the Florida Keys and offers packages that include accommodations, meals, kids’ activities, water sports, and access to the Dolphin Connection program, where guests can interact with dolphins. The resort sits on Duck Key amid 60 acres of pristine property.
With nine distinct accommodation options to choose from, you can find the one that caters to your every need; from suites with up to three bedrooms and full kitchens to villas featuring personal plunge pools. Kids love the dolphin encounters. And the adults? They can’t get enough of the deep-sea fishing and snorkeling tours that make this resort feel like a tropical paradise without leaving the continental United States.
Westgate River Ranch Resort & Rodeo
An authentic Florida dude ranch nestled in one of the few untouched pieces of Florida wilderness, Westgate River Ranch lies just one hour south of Orlando and features a variety of Florida cowboy-themed accommodations. The kids can experience a taste of the Wild West without traveling to Montana.
The accommodations at Westgate River Ranch stay true to the theme, with cabins, teepees, and tents. There are horseback riding lessons, fishing, swamp buggy rides, and even a petting zoo for younger children. Saturday nights bring authentic rodeo shows. Nothing quite prepares you for watching kids cheer on barrel racers under the Florida stars.
Jules’ Undersea Lodge
Jules’ Undersea Lodge is the only hotel where you must scuba dive to your room. Located in Key Largo, this converted research facility sits 21 feet below the surface of Emerald Lagoon.
The underwater adventure begins before you even check in. The view from the 42-inch circular bedroom window is breathtaking, so much so that guests can see the richness of marine life and artificial reefs. Don’t miss the iconic pizza delivery—brought to your room by a scuba diver! Children must be certified divers or complete a brief training session. But trust us—watching angelfish swim past your bedroom window makes every minute of preparation worthwhile.
Historic Lakeside Inn
The Lakeside Inn, which opened in 1883, is the rare historic hotel that didn’t close during the Depression or WWII. With its big porch, fireplace in the lobby, and rocking chairs overlooking the lake, this inn looks like it could be in New England. Located in Mount Dora, this charming retreat offers families a taste of Old Florida elegance.
With brightly hued yellow buildings set among towering, moss-draped oak trees and exquisitely landscaped grounds that curve down to meet Lake Dora, the Inn has welcomed numerous dignitaries and celebrities, including President Calvin Coolidge. The Sunday brunch here remains legendary.
Katie’s Kaboose
Katie’s Kaboose is a renovated train caboose equipped with a full-sized bed and a single trundle bed. The caboose has a full kitchenette, a full-size bed, a functional bathroom, and a lovely deck with a charcoal grill and a fire ring. Located at Adventures Unlimited in Milton, this unique accommodation lets families live out their Boxcar Children fantasies.
After a day of zip-lining and tubing on Coldwater Creek, kids can roast marshmallows by the fire ring. The smell of wood smoke mixing with pine trees creates memories that last long after checkout.
Don CeSar Hotel
There’s no mistaking the Don CeSar. Instantly known as Florida’s Pink Castle when it opened back in 1928, this ten-story hotel sits on the sugary sands of St. Pete Beach, an island in the Gulf of Mexico. This iconic “Pink Palace” has welcomed families for nearly a century.
The hotel’s rosy facade catches the Gulf Coast sunlight in ways that make even smartphone photos look professional. Kids spend hours building sandcastles on the pristine beach while parents sip cocktails at the beachside bar. The hotel offers family-friendly amenities including pools and supervised children’s activities.
Treehouse Cabin Retreat
Welcome to The Treehouse Cabin Retreat, where time stands still and nature takes center stage. Nestled in nature-based Old Town, Florida, our rustic oasis is your invitation to unplug, unwind, and rediscover the simple joys of life. This five-acre wooded property offers both treehouse and cabin accommodations near the Suwannee River.
Roast marshmallows and share stories by the large fire pit, sway in the hammock as you lose track of time, challenge your family to outdoor games, and explore the enchanting trails that wind through almost 5 acres of woods. The property provides:
- Nature trails for hiking
- Fire pits for evening gatherings
- Hammocks for afternoon naps
- Outdoor games for family fun
Casa Monica Resort & Spa
Casa Monica opened in 1888. St. Augustine’s Casa Monica Resort, originally named the Cordova Inn, was Henry Flagler’s first hotel. It’s appreciated today for its frescoes, fountains, and convenient location in the center of the historic district. This Moorish-style masterpiece transports families to another era.
Originally built in 1888, Casa Monica is nestled in the heart of St Augustine’s historic district. It’s a grand, Moroccan-themed hotel that makes you feel like you’ve been transported to northern Africa. The hand-painted tiles and carved wooden details provide countless photo opportunities. Kids love exploring the castle-like corridors while parents appreciate the full-service spa.
Headwaters Jupiter
At Headwaters Jupiter, guests reside in their own private retreat. The main lodge is made up of three up-cycled shipping containers, and is surrounded by native Florida plantlife, edible gardens, and other thoughtfully designed landscape elements. This eco-friendly glamping experience accommodates up to eight guests.
There are eight bikes, two canoes and four kayaks—ready to help you explore. There are two bedrooms upstairs with a shared bathroom and balcony; downstairs, there is one bedroom and bathroom with a full kitchen, dining, and seating area, and an open wooden deck. The property sits just 20 miles north of Palm Beach, making it perfect for families who want nature without isolation.
Florida House Inn
This 17-room inn is in the heart of Fernandina’s historic district. It was built in 1857 and claims to be the oldest continuously operating inn in Florida. Located on Amelia Island, this historic gem offers families a chance to experience authentic 19th-century Florida hospitality.
The inn maintains its historical character while providing modern family amenities. Victorian-era furnishings fill the common areas, and the wide front porch invites evening conversations. Fernandina Beach’s shops and restaurants lie just steps away.
Grand Tiki floating suite
If you truly want to get off the grid, you need to book this floating tiki hut! You’ll think you have been transported to Tahiti in this beauty. It features a large king suite with French doors looking onto a floating deck, in the middle of the sea. This Keys accommodation literally floats in crystal-clear waters.
Sipping your morning coffee, surrounded by the crystal-clear waters of the Florida Keys, is about as oceanfront as you can get. Amenities include paddleboards, snorkeling gear, Wi-Fi, sunset hammocking, and voice-activated lighting. Tropical teak floors meet endless ocean views. Not great for families with very young children, but perfect for those with adventurous teens.
Island Escape
Island Escape is an Airbnb accommodation near Georgetown, Florida. The gorgeous villa floats in the St. Johns River, on a five-acre lot, that is only accessible by boat. It’s the perfect hideaway for watersports lovers and those who want a little privacy on their vacation. This private island getaway offers the ultimate in family seclusion.
Reaching the property requires a short boat ride, which immediately sets the tone for adventure. The villa provides all modern conveniences while maintaining that castaway island feeling. Kids can fish from the dock while parents enjoy uninterrupted sunset views.
The Driftwood Resort
Owner Waldo Sexton built his sprawling Driftwood Inn of cypress logs and pecky-cypress paneling from the swamps around Blue Cypress Lake, some 26 miles away. Established in 1935 by prominent figure Waldo E. Sexton, this beachfront resort boasts of being a part of the National Registry of Historic Places. Located in Vero Beach, this quirky resort defies conventional hotel design.
Inside, the Inn was filled with quirky objects Waldo found on gathering forays domestically and abroad, including ship’s wheels, cannons, old chests, and a menagerie of old bells that guests are invited to ring today. The architecture seems to follow no particular plan—balconies appear everywhere, nothing seems quite square. It’s wonderfully chaotic in the best possible way.
The Grove Resort & Water Park
After a fun day sploshing and splashing, you can unwind with your tired little ones in one of the Grove’s spacious two or three-bedroom suites. These suites are perfect for families as they are three times larger than a typical hotel room. This Orlando-area resort features Surfari Park with the FlowRider surfing simulator.
Rooms come equipped with full kitchens, washer/dryers, and multiple bathrooms with tubs. The Springs Grill is a great choice, where you can enjoy your meal in their delightful patio setting. The water park keeps kids entertained for hours while spacious suites provide room for everyone to spread out. Could be worse than having your own washer and dryer on vacation. Actually, it couldn’t.
Seminole Chickee Huts
If you’re looking for a blast from the past, head for Ochopee and book a night in a traditional Chickee-raised bungalow. These cabins on stilts are built in the traditional style of the Seminole and Miccosukee Tribal people who make the Everglades their home. These authentic structures offer families a unique cultural experience.
They tower over swamps and grassland, giving incredible views of Everglades National Park. Park it on the deck for the most phenomenal sunset you have ever seen as you watch flocks of birds flying overhead. The cabins are primitive but provide an unforgettable connection to Florida’s indigenous heritage. Wildlife photographers consider this location unmatched.
Beyond the ordinary
— Photo by djulia86@gmail.com
Florida’s unique accommodations prove that where you stay can be just as memorable as where you go. From underwater hotels to floating tiki huts, these properties offer families the chance to step outside their comfort zones and create stories worth telling for years to come.
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