Search
Resorts & LodgesVacation RentalsDeals & PackagesTravel Guides
List Your Property
It’s around this time of year we notice that parents either wear a frenzied facial expression or their eyes are still, empty pools of exhaustion. Summer was bad enough, when no school meant the kids ran havoc throughout the house. Now, with snow piled high outside your door, the children refuse to venture out into the backyard tundra. Instead, the living room and kitchen serve as military bases engaged in a pivotal battle. If you can save your made-from-scratch bread dough from being catapulted, and manage to find time to peruse our list of Top 10 Florida Keys Family Vacation Resorts, the screams in the background will fade into laughter beneath a palm tree. At any of our Sunshine State resorts, the lush Keys islands provide secluded tranquility along with a variety of activities as expansive as the surrounding gulf and ocean waters.
1

Barefeet Rentals

Key Largo, Florida

View
Website
call direct
+1 (866) 599 - 3095

For any budget, occasion, and party size, Barefeet Rentals is the Keys' destination of choice!

There's simply so much to do here! Whether your family is interested in exhilarating adventure or serene... read more

For any budget, occasion, and party size, Barefeet Rentals is the Keys' destination of choice!

There's simply so much to do here! Whether your family is interested in exhilarating adventure or serene relaxation, they have a cornucopia to choose from. Charter a boat for snorkeling the coral reefs, dive shipwrecks, swim with dolphins, and catch the big one on a deep sea fishing excursion! Explore the nearby everglades for a unique and unforgettable eco-adventure. You'll see manatees, birds, and alligators up close and personal (but from a safe distance, of course). As the evening wanes, you'll set sail on a sunset cruise or just dig your toes in the sand and relax watching the gorgeous sunset!

Address

103400 Overseas Hwy #203, Key Largo, FL 33037

Related activities

Vacation rentals are just a short drive from Islamorada, and are surrounded by beachfront views of the Atlantic and the calm waters of the northern Gulf of Mexico, known locally as Florida Bay.

Fun facts

Key Largo is an island in the upper Florida Keys archipelago and is the largest section of the Keys, at 33 miles long.

close
2

Hawks Cay Resort

Duck Key, Florida

View call direct
+1 (888) 443 - 6393

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... read more

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.

Address

61 Hawks Cay Boulevard Duck Key, FL 33050

Elevation

3 ft

Highlights

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.

close
3

Coral Bay Resort

Islamorada, Florida

View
Website
call direct
+1 (888) 328 - 0454

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,... read more

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!

Address

75690 Overseas Highway Islamorada, FL 33036

Population

6,184

Highlights

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.

close
4

Chesapeake Beach Resort

Islamorada, Florida

View
Website
call direct
+1 (866) 588 - 0250

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... read more

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.

Address

83409 Overseas Highway Islamorada, Florida Keys 33036

Related activities

Explore the beauty of nature at Lignumvitae Key Botanical State Park.

Fun facts

The name Islamorada, meaning "purple island", came from early Spanish explorers in the area.

close
5

La Jolla Resort Hotel

Islamorada, Florida

View
Website
call direct
+1 (877) 574 - 9062

Treat your family to luxury, fun, and natural majesty all in one package! La Jolla Resort Hotel is set in a vintage 1950's Florida style, but also comes with all the modern amenities you'd expect!

From the... read more

Treat your family to luxury, fun, and natural majesty all in one package! La Jolla Resort Hotel is set in a vintage 1950's Florida style, but also comes with all the modern amenities you'd expect!

From the cozy confines of LJRH you have easy access to the island's plethora of attractions and activities, both natural and man-made. You're just moments away from many of Islamorada's restaurants, activities, and, of course, beaches, so should the mood strike you take a leisurely stroll and treat yourself. For the more adventurous, take a complimentary bicycle, kayak, or paddleboard and do some island exploring, or rent a boat and go a little deeper! La Jolla's friendly and informative staff is always available to help you plan your days or assist you in whatever capacity you require!

Address

82216 Overseas Hwy Islamorada, FL 33036

Highlights

Each uniquely designed building includes no more than five guest rooms, so you know you're getting a personalized experience!

Fun facts

The name Islamorada (Original meaning: "Island Home" after the Pinder family schooner of that name) came from early Spanish explorers in the area.

close
6

Parrot Key Resort

Key West, Florida

View
Website
call direct
+1 (866) 939 - 3715

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... read more

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.

Address

2801 N Roosevelt Blvd, Key West, FL 33040

Population

24,649

Elevation

18 ft.

close
View
Website
call direct
+1 (866) 452 - 5369

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... read more

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!

Address

2600 Overseas Highway, Marathon, FL 33050

Population

10,255

Elevation

3 ft

close
8

At Home in Key West

Key West, Florida

View
Website
call direct
+1 (877) 695 - 2791

Few places in the US feature the amount of tropical beauty and superb rental companies that Key West does. At Home in Key West is simply the best of the best!

A veritable Mecca for sun and fun seekers, Key... read more

Few places in the US feature the amount of tropical beauty and superb rental companies that Key West does. At Home in Key West is simply the best of the best!

A veritable Mecca for sun and fun seekers, Key West is ideal for both families and couples looking for a romantic escape. Whatever your reason for visiting, your At Home in Key West property will combine luxury with location to great effect. After you get settled into your spacious and cozy property, simply step out the door and survey the plethora of options available to you. Sample the local Caribbean cuisine, head out on a deep sea fishing trip, or simply relax on the beach and catch a tan. Whatever you do, it'll be an unforgettable experience with At Home in Key West!

Address

905 Truman Avenue, Key West, FL 33040

Related activities

Visit the Key West Aquarium or Turtle Kraals to get personal with the local ocean life or Mel Fisher’s Treasure Salvors Museum to see real treasure rescued from the ocean depths!

Fun facts

At Home in Key West has been managing property in Key West since 1997!

close
View call direct
+1 (800) 937 - 8461

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... read more

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.

Address

245 Front St., Key West, FL 33040

Related activities

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.

close
10

Coconut Cay Resort & Marina

Marathon, Florida

View call direct
+1 (305) 289 - 7672

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... read 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!

Address

Overseas Hwy. Marathon, FL 33050

Highlights

With a marina located on site, Coconut Cay makes it easy to go boating or fishing.

Related activities

Want to get up close and personal with sea turtles? Visit Marathon's turtle hospital for a tour!

close
statsstats