Offering year-round balmy temperatures and a wealth of attractions, these top Florida Keys resorts are ideal for family vacations and multigenerational trips.
The Florida Keys archipelago is known for its stunning natural beauty, beautiful aquamarine waters, endless watersports and spectacular sunsets. The subtropical island chain is loaded with history, wildlife and outdoor adventure experiences. For family groups seeking a gorgeous slice of paradise, this fantastic string of islands offers superb resorts and engaging activities for all ages and interests.
The Florida Keys are a perfect place for families to reunite for a stress-free island vacation in the United States. While the Florida Keys have a relaxed tropical island vibe, no passport is needed to enjoy this stunning destination. It’s easy to reach the Florida Keys by car, plane or a short ferry ride from mainland Florida.
Finding the right place to reconnect in the Florida Keys is essential. While the islands share a laid-back vibe, each has its own attractions. The Florida Keys offer outstanding resorts to fit a wide range of travel budgets, and family-friendly vacation rentals are also available.
Here are 15 top-notch resorts for family vacations in the Florida Keys.
Sunset Key Cottages – Key West, Florida
Sunset Key Cottages is a lovely setting for a family group vacation, multigenerational celebration or fun-filled reunion. Located on a 27-acre private island just minutes from Key West, this idyllic resort features 40 luxurious cottages, a beautiful white sandy beach, dining venues, the Spa at Sunset Key, and a wide variety of other amenities.
The resort’s charming cottages have fully equipped kitchens and most have two-to-four bedrooms. Families will enjoy Sunset Key’s large pool, tennis and basketball courts, and activities for all ages. The attractions of nearby Key West are easily accessible via the resort’s complimentary private shuttle service.
Hawks Cay Resort features a large saltwater lagoon and a wide variety of family-friendly activities. (Photo credit: Hawks Cay Resort)
Hawks Cay Resort – Duck Key, Florida
Hawks Cay Resort is a AAA Four Diamond property set on secluded Duck Key in the Middle Florida Keys. The 60-acre destination resort offers 177 spacious guest rooms and 210 two- and three-bedroom villas ideal for family groups. Hawks Cay Resort features six restaurants, a full-service marina and an endless array of watersports, charter excursions and recreational activities.
Hawks Cay Resort is a popular choice for multigenerational vacations and reunions. Families enjoy the property’s five swimming pools, Tiki Beach and massive saltwater lagoon, racquet sports, an onsite Dolphin Connection program, and the outstanding Calm Waters Spa. Families rave about Hawks Cay’s outstanding kids and teens club activities at Coral Cay, the resort’s activities and adventures center.
Baker’s Cay Resort Key Largo – Key Largo, Florida
Conveniently located in the Upper Florida Keys, Baker’s Cay Resort is part of the Curio Collection by Hilton – a plus for those wishing to earn or redeem points. Formerly a historic pineapple plantation, this 15-acre seaside property features multiple restaurants and 200 well-designed guest rooms and suites, some with lovely water views.
This large resort has fun activities appealing to both adults and kids. Families can enjoy the property’s watersports, pool, beach areas, tennis courts, and various activities including painting classes, scavenger hunts, and movie nights. Cay Kids specials and other family-focused offers are available on select dates.
Isla Bella Beach Resort –Marathon, Florida
Set on over 24 oceanfront acres in the Middle Florida Keys, Isla Bella features several dining venues, five oceanfront pools, a sandy beach area, complimentary bike rentals, miniature golf, and a large fitness center and spa. Families can take part in a full calendar of activities as well as Isla Bella marina watersports and excursions.
With more than a mile of waterfront property and an innovative design, Isla Bella Beach Resort offers gorgeous ocean views from every room and suite. All of the resort’s accommodations are equipped with outdoor terraces, and some have multiple bedrooms as well. Dog-friendly rooms are available.
Cheeca Lodge has long been a favorite for vacationers who enjoy fishing, watersports and family fun. (Photo credit: Cheeca Lodge)
Cheeca Lodge & Spa – Islamorada, Florida
Since 1946, families have flocked to Cheeca Lodge for vacations, reunions and multigenerational getaways. Situated on a 27-acre private estate in the “Sportfishing Capital of the World,” Cheeca Lodge features a wide variety of luxurious rooms, suites and villas – including 43 new oceanfront suites. The private villas, called The Casitas at Cheeca Lodge, are well-suited for families and multigenerational groups.
Guests at Cheeca Lodge can enjoy multiple pools and distinctive dining venues, a Jack Nicklaus-designed golf course, tennis and sports courts, fun-filled activities and a state-of-the-art spa and fitness center. The resort is known for its outstanding watersports and excursions, as well as its Camp Cheeca program for kids.
Playa Largo Resort & Spa – Key Largo, Florida
Playa Largo Resort is part of Marriott’s Autograph Collection, which makes it particularly attractive for families seeking to use hotel loyalty program points in the Florida Keys. Conveniently located on 14.5 acres in the Upper Florida Keys near John Pennekamp Coral Reef State Park, the luxurious waterfront property features upscale rooms, suites, villas and a private beach house.
Amenities and attractions include a pool and beach area, four restaurants, a spa, and watersports at the private marina. Guests can also have fun while participating in Playa Largo’s family activities, ecotours, and classes.
Southernmost Beach Resort – Key West, Florida
Set at the end of Duval Street, Southernmost Beach Resort keeps families happy with a wide variety of amenities and easy beach access. Guests can choose from spacious rooms and suites with island, pool or oceanfront views, and group blocks are available for reunions and multigenerational celebrations.
Amenities at the six-acre property include three heated pools, bike rentals, dining venues, and entertainment options. Two beaches are available as well. Southernmost Beach Resort is just a stroll away from many Key West attractions, including Southernmost Point, the Key West Aquarium, Mel Fisher Maritime Museum and Key West Butterfly & Nature Conservatory.
The freshly reimagined Islander Resort is unveiling updated accommodations and new amenities. (Image credit: Islander Resort Islamorada)
Islander Resort Islamorada – Islamorada, Florida
The recently renovated Islander Resort Islamorada is debuting a new era this year, offering many innovative features, attractions, and experiences. Situated on 24 acres stretching from ocean to bay, the 114-room property includes fully refreshed beachfront suites, bungalows with beautiful ocean views, and townhome-style Bayside Villas with two bedrooms and adjacent boat slips.
The Islander Resort’s multiple dining outlets feature locally inspired culinary offerings, and several new restaurants and bars are opening this year. Families can enjoy many activities at the newly transformed property, including beach movie nights, watersports, fishing adventures, bocce ball and a seaside putting course.
Hampton Inn Key Largo – Key Largo, Florida
The moderately priced Hampton Inn Key Largo is located within half a mile of John Pennekamp Coral Reef State Park, America’s first undersea park. The resort features family-friendly accommodations with balconies or patios, confirmed connecting guest rooms, microwaves, mini-fridges, and free WiFi.
Families will enjoy the Hampton Inn’s large pool, beach, and fitness center. A complimentary hot breakfast is served daily. The property participates in the Hilton Honors loyalty program.
Parmer’s Resort – Little Torch Key, Florida
Families can relax and unwind together at Parmer’s Resort in the Lower Florida Keys. The property is set on five acres on Little Torch Key and consists of guest rooms, efficiency studios, suites and cottages. Some have full kitchens and water views. Parmer’s Resort offers full resort takeovers for family reunions and events.
The dog-friendly property features a small beach area, outdoor heated pool, on-site boat slips, complimentary continental breakfast, free kayak and paddleboard rentals, and lawn games. The National Key Deer Refuge and popular Bahia Honda State Park are nearby, and Key West is just 25 miles away.
Tranquility Bay’s two- and three-bedroom beach villas are perfect for families and multigenerational groups. (Photo credit: Tranquility Bay Beachfront Resort)
Tranquility Bay Beachfront Resort – Marathon, Florida
This tropical 12-acre resort is an idyllic paradise where family members can fill their days with endless activities or simply relax and do nothing at all. Tranquility Bay’s 87 two- and three-bedroom beach villas with Gulf of Mexico views are ideal for reunions and family group getaways. Guest rooms are also available.
Tranquility Bay’s fun-filled attractions include a 2.5-acre white sand swimming beach, three pools, a wide variety of on-site watersports, Nicklaus Design putting green, beach volleyball court and fitness room. Guests can dine at the resort’s highly rated Butterfly Cafe and enjoy craft cocktails and live evening entertainment at beachfront TJ’s Tiki Bar.
Pines and Palms Resort – Islamorada, Florida
Set on four tropical acres studded with over 100 coconut palms, the boutique-style Pines and Palms Resort offers recently remodeled rooms and newly renovated cottages. The property’s charming beach cottages have full kitchens, and some feature multiple bedrooms.
Families can enjoy the resort’s beach area, oceanfront heated swimming pool, bike and kayak rentals, poolside entertainment, boat charters and swimming off the resort’s piers.
Hyatt Centric Key West Resort and Spa – Key West, Florida
The Hyatt Centric Key West is situated on the waterfront near Duval Street, providing convenient access to Key West’s many attractions. The luxury resort’s spacious rooms feature private balconies and mini-fridges, and some offer stunning views of the Gulf of Mexico.
Guests can enjoy the Hyatt Centric Key West’s dining venues, heated outdoor pool, watersports and excursions, and the Jala Spa and fully equipped fitness center. Hyatt loyalty program members can earn or use their points at this pet-friendly property.
Families staying at Amara Cay Resort can play at all three Islamorada Resort Collection properties in the area. (Photo credit: Nancy Schretter)
Amara Cay Resort – Islamorada, Florida
Family groups can triple their fun while vacationing at Amara Cay Resort. The boutique resort is part of the Islamorada Resort Collection, which operates three properties in Islamorada. Families staying at Amara Cay can access the amenities at its two sister resorts, including beach areas, pools, restaurants, watersports, boat slips and more. A free shuttle and water taxi are available for guests.
Once at Amara Cay Resort, however, families may want to stay and play. The property features a beach area, heated zero-entry pool, fitness center, marina, and variety of boating excursions. Complimentary kayaks, paddleboards and bikes are available.
Glunz Ocean Beach Hotel & Resort – Key Colony Beach, Florida
Set on the soft sands of Key Colony Beach and close to Marathon’s attractions, Glunz Ocean Beach Resort offers families many activities and experiences. The beachfront resort features 51 rooms, suites, and multi-bedroom villas with refrigerators, WiFi and microwaves.
Families can enjoy the property’s two oceanfront pools, kayaks, paddleboards, beach cruiser bicycles and fire pits. Other popular amenities include the oceanside restaurant, outdoor BBQ facilities, a guest laundry and waterfront gym.
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By Nancy Schretter, Contributing Editor
Header Photo Credit: Cheeca Lodge
