With an exotic location like Islamorada, our No. 1 Florida Keys pick sets the stage for an opulent tropical getaway. We know that’s not the typical first line you see under family vacations, but Cheeca Lodge and Spa surprised us with its ability to blend adult-friendly leisure with kid-friendly fun.
In operation since 1946, Cheeca Lodge is well versed in luxury Florida Keys getaways. Immerse yourself in the West Indies style, with palm leaf fans, cheery wood furnishings and floor-to-ceiling views of the 1,100 ft. stretch of beach radiate a warmth that rivals the coastal sun’s rays. Plus, with a screened in-balcony, a marble bathroom with an oversized soaking tub and a breakfast bar looking into a fully-equipped kitchen, there’s a place and ample space for the whole family. When you’re not judging the sandcastle contest or making a sand angel, enter a world of cascading waterfalls and aquamarine pools surrounded by vibrant foliage. No, you’re not in uncharted Florida jungle, you’re at the Spa at Cheeca Lodge! Cleansing salt scrubs and the massaging waters of a Vichy shower are just a few of the ways to refresh your spirits before returning to family beach time.
Islamorada is the Sportfishing Capital of the World with an impressive 600 species of fish inhabiting the Florida Bay and Atlantic Ocean waters. Cheeca Lodge and Spa offers a 525-ft. pier from which the avid angler can cast a line.
Related Onsite Offerings
Camp Cheeca is a kids-only club at Cheeca Lodge for fun-filled Florida family trips. Besides fishing off the pier, kids will explore the beach, swim in a lagoon and learn how to snorkel!
While the kids are at Camp Cheeca, you can savor a plate of sushi and a flight of sake at Nikai Sushi without having to hear the kids complain that the raw fish is too wiggly.
Add a touch of luxury to your family's Florida vacation with Hawks Cay Resort in Duck Key, Florida.
Hawks Cay Resort is a luxurious place for your family vacation in the Florida Keys. Their spacious rooms and villas offer all the space of home alongside luxurious amenities. With classic West Indies and Caribbean decor and bright colors, they're the perfect place for your family to stay in the Florida Keys. But all that luxury doesn't mean you'll have to sacrifice the fun of your vacation! Kids and adults alike will find a variety of activities available both on site and nearby when they stay at Hawks Cay Resort. Swim with bottlenose dolphins. Go snorkeling. Splash in one of five on site pools. All this and more awaits you at Hawks Cay Resort.
61 Hawks Cay Boulevard Duck Key, FL 33050
If you need to spend some time apart, your kids can enjoy spending time with people their own age at special "Kids Night Out" parties.
Spend your Florida Keys vacation on the shore with Coral Bay Resort.
Enjoy the old-fashioned family fun of a day on the beach with Coral Bay Resort! The cottages from Coral Bay are right on the shore, putting the soft white sand and blue water just steps from the door. Enjoy all the comfort of home in your private cottage with the convenience of a beach location. More than just a day at the beach, Coral Bay Resort puts the family fun of Islamorada just a short distance away! Go snorkeling in the water, take an eco tour, or swim with dolphins, stingrays, and sea lions at Theater of the Sea!
75690 Overseas Highway Islamorada, FL 33036
A day on the seaside is just steps away at Coral Bay Resort! The soft white sand of the beach is right outside your door.
Chesapeake Beach Resort offers you everything you want on your vacation to Islamorada, Florida: a variety of exciting activities, comfortable and homey rooms, and plenty of modern convenience.
Chesapeake Beach Resort stands on 6.5 acres of oceanfront sands and gardens halfway between Miami and Key West. This beautiful property offers a wide variety of guest rooms and villas, so you're sure to find a lodging option to suit your need. Each one comes with all the touches you want on your vacation: wireless internet, updated interiors, and more! On site and around Islamorada, you will find a wide variety of great activities perfect for the whole family. Splash in one of two heated pools on site. Nearby, try fishing, visit the soft white sand of the beach, or splash in the ocean. All this and more awaits you at Chesapeake Beach Resort.
83409 Overseas Highway Islamorada, Florida Keys 33036
Explore the beauty of nature at Lignumvitae Key Botanical State Park.
The name Islamorada, meaning "purple island", came from early Spanish explorers in the area.
The verb in our No. 5 spot’s name may make you cringe as memories of cracking down on the kid’s dinner etiquette come flooding back to you. Too many times you’ve seen glasses of juice and boats of gravy knocked onto the good tablecloth because your little one decided to reach instead of ask.
Luckily, etiquette faux pas are non-existent at The Reach Resort. In fact, dinners will seem practically flawless at the onsite Strip House restaurant. Despite the coy connotation, its name refers to the juicy strips of choice steaks found inside its elegantly red, patterned walls. Of course, seafood also graces the menu along with a healthy helping of unique side dishes such as black truffle creamed spinach and creamed corn with pancetta. And no one will fault you for reaching for seconds. As part of the Waldorf Astoria Collection, just like our No. 2 pick, you can expect quality private accommodations and abundant activities to keep your family comfortable and entertained. With the same trademark emphasis on soothing island ambiance and high-class luxury, ocean view rooms, boutique suites and spacious luxury suites treat the family to an unforgettable Florida Keys stay.
1435 Simonton St., Key West, FL 33040
Making full use of the aquatic playground right outside its doors, The Reach Resort offers waverunners, kayaks, windsurfers and snorkeling gear for rent. You can also take a deep sea, light tackle or flats charter sportfishing trip.
The “Mangrove Hole” on Key West Golf Course is a challenge worthy of a skilled opponent. Not far from The Reach Resort at Key West Golf Club, you can test your ability on this 143-yard, par-3 hole.
Family fun is waiting for you at Parrot Key Resort!
Just minutes from historic Old Town in Key West, Parrot Key Resort puts the fun of Key West at your fingertips. Spend a day splashing in the ocean and building sandcastles on the beach. Wander the sculpture gardens. Take an eco tour or go snorkeling. At the end of a day of adventure, retire to your comfortable room at Parrot Key Resort. The resort's rooms offer space enough for the whole family. Whether you want a cozy one-bedroom suite or the added space of two bedrooms, the perfect lodging for your family is waiting at Parrot Key Resort.
2801 N Roosevelt Blvd, Key West, FL 33040
Make Tranquility Bay Beach House Resort your home away from home in the Florida Keys.
Located in Marathon, Florida, Tranquility Bay Beach Resort is an ideal location for your next family vacation. These fully furnished beach houses offer up to three bedrooms and all the convenience of home in a great Florida Keys location. Just outside your door, you will find the soft beach sand that makes the Florida Keys a world-famous vacation destination. Play at the beach, build a sandcastle, or splash in the water. You can also enjoy watersports, get a relaxing massage, and much more. It's all waiting for you at Tranquility Bay Beach House Resort!
2600 Overseas Highway, Marathon, FL 33050
Make a splash with a family trip to Islander Bayside Resort!
Set amid lush tropical foliage are the five cottages of Islander Bayside Resort. These cottages offer you and your family the utmost in privacy during your Florida Keys getaway. Equipped with gourmet kitchens featuring top-of-the-line stainless steel appliances and granite counter tops and other touches like flat screen televisions and private balconies, Islander offers you all the comforts of home with just the right touches of luxury. And, with the sea so close, you're never far from exciting activities. Spend a day on the beach splashing in the water or working on your tan. Walk or bike to nearby boutique shops, restaurants, historical sites and museums. Islander Bayside can help you arrange all this and much more for a vacation you will never forget.
81450 Overseas Hwy Islamorada Fl 33036
At the peak of summer, the average high in Islamorada is a comfortable 89° F.
Need a break from the excitement of diving? Why not visit The Florida Keys History of Diving Museum with your family.
Key West, Florida
CALL DIRECT: +1 (877) 564 - 1273
While connecting rooms at a hotel a few miles from the beach seems like a good compromise on your family getaway, shouldn’t have to live with compromise. Especially when this Westin Resort will strive to fulfill every single desire of yours.
Sunset Key Guest Cottages, A Westin Resort offers 27 remote, pristine cottages with whitewashed walls and Old Florida furnishings. What makes these quaint accommodations even more idyllic is their location on the 27-acre Sunset Key island. Taking up seven of these acres, your one, two or three-bedroom cottage has ample space inside and out. Always steps from the sapphire ocean waves, you’ll wonder how the family arrived in the Caribbean without showing your passports. Enjoying the privacy of a guest cottage doesn’t mean you have to forsake resort-style amenities. Take a dip in the oasis-like zero-depth entry pool, make a serve on one of the tennis courts, request a private chef or dine out at the beachfront restaurant, Latitudes. For a satisfying end to the day, sit back and relish a golden Florida sunset in the Adirondack chair on your front porch.
245 Front St., Key West, FL 33040
On a list of 25 things to do in Key West, activities include throwing a coin in the fish mouth of Captain Tony, see a six-toed cat in Ernest Hemingway’s house, grab a dish of gelato or a slice of key lime pie, visit Dry Tortugas National Park and more.
Related Onsite Offerings
Inside your Sunset Key cottage you will find a complimentary breakfast basket filled with muffins, orange juice and other baked goods, along with a newspaper. Also provided are bathrobes, Starbucks coffee, Tazo tea, flatscreen cable TV, complimentary wireless Internet and more.
Enjoy old-fashioned family fun on the seashore with Coconut Cay Resort.
Located just off the soft white sand of the beach, Coconut Cay Resort is a perfect family destination in Marathon, Florida. With the beach just outside your door, it's easy to spend a day on the sand, splash in the water, or fly a kite! More than just beach fun, Coconut Cay Resort makes it easy to explore the water in other ways, too! Snorkel among brilliant tropical fish. Charter a boat and go fishing. Visit the wildlife at several nearby attractions like the turtle hospital. All this and more awaits you!
Overseas Hwy. Marathon, FL 33050
With a marina located on site, Coconut Cay makes it easy to go boating or fishing.
Want to get up close and personal with sea turtles? Visit Marathon's turtle hospital for a tour!