9 Key West Family Resorts | Capture the Spirit of the Young at Heart

Designed by American industrialist Henry Flagler, Casa Marina is the grand dame of Key West hotels. Originally opened in 1920, the 311-room property still holds its own with other historic Florida gems like The Breakers and The Don CeSar. Another superlative: It boasts the island’s largest private beach (1,100 feet).

Presidents and Old Hollywood celebrities once roamed the halls. Now it’s primarily families who take advantage of amenities like children’s menus, cribs, high chairs, and babysitting services for when you want to hit the spa or zoom around the island on Jet Skis. The whole crew can enjoy activities like sand-sculpture workshops and scooter rentals.

Action centers on the resort’s two oceanfront pools, but even more family fun is on deck at the neighboring Clarence S. Higgs Memorial Beach Park, featuring volleyball, pickleball, and a playground. After an active day, return to the hotel’s surprisingly casual Sun Sun restaurant for dinner favorites from burgers to Gulf-shrimp fettuccini just steps from the waves.

Renovated to the tune of $25 million in January 2019, the Parrot Key Hotel is a 148-room hideaway luring families with its selection of airy two-bedroom suites and three-bedroom villas (one-bedroom suites and standard guest rooms are also available). Upgrade to the Waterfront Experience for even more convenience—think early check-in, late check-out, and a custom beach bag filled with essentials like sunscreen and sand toys. The revamp also introduced The Grove Kitchen & Bar, where the gang can munch on casual grub like burgers, pizzas, and wraps before indulging in Key lime pie on a stick.

The resort doesn’t have a private beach but will shuttle your tribe to Smathers Beach two miles away from where chairs (gratis) and beach rentals (paddleboards, kayaks, umbrellas) await. A complimentary resort shuttle also runs to Duval Street until 4 p.m. (Word to the wise: Kids under five need a car seat to ride.)

The Ocean Key Resort & Spa is a 100-room Noble House Resort. It could just rest on its laurels—namely, its prime location overlooking the harbor and directly adjacent to legendary Mallory Square. But the property extends some handy perks for families as well, from children’s menus, high chairs and Pack ‘n Plays available on request to a laundry room and kids mani-pedis at the spa.

Shade the little ones in a cabana at the pool (first come, first served), where attendants occasionally come around with sweet surprises like frozen fruit. Or stroll to a pickup location for the Old Town Trolley, a hop-on, hop-off ride that passes more than 100 local attractions. The resort is also a departure point for Fury Water Adventures; choose from excursions like snorkeling, eco-tours and sunset sails.

When the night begins to fall, the nightly Mallory Square Sunset Celebration—complete with artists and street performers—is the place to be. After all the excitement, a colorful Ocean Key junior suite with a whirlpool marble bathtub offers a comfy space for your clan to crash.

Set on a 27-acre island 500 yards off Key West, Sunset Key Cottages starts the adventure as soon as your brood boards the resort’s ferry launch on Front Street. The property has changed hands several times since opening in 1998 (it’s been a Hilton and a Westin and is now part of the Opal Collection), but the 40 luxury cottages have always catered to families looking for space and seclusion.

Spread out in one-, two-, three- and four-bedroom cottages, each with a tin roof, wraparound veranda and full kitchen; the largest also come with a plunge pool. The kids will get excited to find a basket of fresh fruit and baked goods on your porch each morning; for even more ease, request your cottage be pre-stocked with your favorite grocery items. Don’t feel like cooking on vacation? There’s also fine dining and a pool bar and grill on site.

If you need a change of scenery from the resort’s pool and private beach, the boat ride to Key West takes only about seven minutes. From there, you can hoof it to attractions like the Mel Fisher Maritime Heritage Society & Museum (treasure, pirates, shipwrecks!) and the Key West Aquarium (100-plus species of fish, turtles, sharks and birds). Just get back to the hotel in time to catch the Conch Cruiser “icicle bicycle” delivering frozen treats to guests every day at 3 p.m.

If your vision of #FamilyVacationGoals includes a smiling portrait beside the iconic buoy marking the Southernmost Point of the Continental United States, the Southernmost Beach Resort is a classic family retreat that puts you within a five-minute walk. That’s definitely a plus when lines for the photo op can snake down the street.

Multi-gen groups feel right at home here thanks to the resort’s laid-back vibe, breezy eatery, live music and colorful Adirondack chairs facing the Atlantic. Plus, plenty of worthy extra-curriculars are right in the neighborhood. Find the island’s best Key lime pie at Blue Heaven restaurant, where bric-a-brac tables are tucked into a shady courtyard. Enter a fluttering utopia at the Key West Butterfly and Nature Conservatory. And soak in the real Florida at Fort Zachary Taylor State Park.

For families eager to get out on the water, the hotel concierge can arrange outings like parasailing and glass-bottom-boat tours. But be sure to leave time for the resort’s Pineapple and Shores pools, as well as its two private beaches, where a little R&R is in order.

When this conch-style boutique debuted in December 2014, it was the first newly built hotel to open in Key West’s charming Old Town in more than two decades. Five years later, The Marker Waterfront Resort still holds that distinction. Despite its location, just three blocks from Duval Street (Key West’s answer to New Orleans’ Bourbon Street), the resort maintains a relatively quiet, upscale vibe, and parents appreciate the full bathtub and balcony in each of the 96 crisp rooms.

On-site bike rentals ($25 per bike, per day) allow families to make the most of the resort’s prime location. Start with a sunscreen run to Key West Aloe; take in the parrot presentation at Nancy Forrester’s Secret Garden (10 a.m. daily); and continue to the oddities of Ripley’s Believe It or Not!

Back at the resort, cool off in a courtyard pool (two of the three are family-friendly). Then stick around for dinner at the hotel’s Cero Bodega restaurant: On Mondays from 4 to 7 p.m., gourmet pizzas are buy one, get one free, and kids get free soda.

Not only is The Gates—arguably Key West’s trendiest property—family-friendly, but it’s pet-friendly too. Four-legged guests are even welcomed with a little box of treats. Premiered in 2015, the 100-room converted motel is awash in reclaimed wood and retro-chic décor, and in lieu of a restaurant, a poolside food truck called The Blind Pig satiates hunger with kid-approved entrees like tacos and sandwiches (also: cupcake “sushi”).

The resort is located a good 15-minute drive from Old Town, but a free hourly shuttle (8 a.m. to 11 p.m.) transports guests to the heart of the action. Plus, families may find that the hotel’s proximity to chains like McDonald’s, Dunkin’ Donuts and Publix Super Market can be helpful in a pinch.

The Gates’ sister property, 24 North, was renovated in 2015 and is located right next door, offers access to its neighbor’s amenities, as well as a few other family-approved features, including a handsome art deco pool and the Toasted Coconut outdoor restaurant (the conch fritters are a crowd-pleaser). Plus, there are eight spacious premium suites (145 rooms total) and a Starbucks. Kids will find small entertaining touches such as beach balls, hammocks, a swing and giant Connect Four, while parents can enjoy weekly programming like karaoke and yoga.

24 North also utilizes the Old Town shuttle—a care-free way to reach all the landmarks downtown. First stop: the popular Cuban Coffee Queen shop next to the shuttle drop-off (order café con leche for the grown-ups; smoothies for the little ones).

Oceans Edge Key West Resort Hotel & Marina is a 20-acre haven—opened in 2017 as Key West’s largest resort—and is all about the water. Set on Stock Island about six miles from Old Town, it boasts its own marina, which means direct access to fishing charters and other excursion boats. Take the whole herd out on a family fishing trip, and bring your catch back to the hotel’s Yellowfin Bar and Grill, whose chef will happily prepare it for dinner. Or head out on a Dolphin Watch Sail with Fury Water Adventures, which prides itself on responsible dolphin observation.

Decorated in natty cobalt and white, the 175 rooms each feature a balcony or patio for admiring the ocean views. Accommodations range from standard guest rooms to two-bedroom suites that sleep up to 10 (Pack ‘n Plays are also available on request). Families can swim in six pools (some with dancing water features), participate in poolside activities, play giant chess and Connect Four, ride bikes (complimentary) and watch outdoor movies.

A daily shuttle transports guests downtown (9 a.m. to 11:25 p.m.), but don’t miss the chance to explore the quaint neighborhood of Stock Island, home to a golf club, a botanical garden, and several tasty restaurants. Hogfish Bar & Grill is a local institution: Go for the fresh seafood, potent drinks, and open-air waterfront dining; stay for the live music on weekends.