Have the Ultimate Family Beach Getaway at Destin Holiday Isle!

A family walking on the beach holding hands.

Everybody has their place. The one that you think about when you need to go to your happy place. The one you can’t wait to return to. One that brings you total bliss. For me, that place is Holiday Isle in Destin, Florida. It’s my favorite spot for a beach getaway, a special celebration, or some relaxing family time. I rented a condo there a few years ago, and ever since, it’s been my dream to own a place on Holiday Isle when I retire. It’s really that beautiful!

I thought I’d share some of my favorite restaurants, shopping, and things to do in and around Holiday Isle with you in order to inspire you to schedule a visit. I promise it’s even better in person!! 

A family is playing on the beach with their children.

Destin Holiday Isle’s History

The history of Destin Isle goes back thousands of years to when Native Americans discovered the natural abundance of seafood in the Gulf and the bay. Everything from shrimp to Mahi Mahi to Flounder and Sea Trout can be found and harvested off of the coast of Destin and are still caught here to this day!

In 1848, Captain Leonard Destin arrived from New England to begin fishing in the area and soon began fishing for commercial purchases. Other fishermen and adventurous tourists soon became interested in the area and eventually began settling and establishing community resources like a church and a post office. By the roaring 1920s, Destin was a popular tourist attraction for those looking to try their hand at deep-sea fishing. 

A family is walking on the beach with their children Destin Holiday Isle.

By the 1960s, high-rise condos and residential development began to pop up on Holiday Isle. Since then, millions of tourists have visited to enjoy Holiday Isle’s spectacular beauty, and others have decided to make it their personal residence. Today, it’s known as the “Crown Jewel” of the Emerald Coast and has recently been named among the Most Beautiful Places in America by Good Morning America, among many other publications. 

If you’ve never been to Destin, it’s time to see what all the hype is about for yourself! It won’t take you long to see why so many people choose Destin as their vacation destination over and over again.  

A family walking on the beach holding hands.

Condo Rentals and Ownership

Staying on Holiday Isle is the kind of vacation experience that people dream about, with white sandy beaches and sparkling water dotted with leaping dolphins. The sunsets are magnificent, and even better surrounded by the people you love most. 

Whether you’re looking to visit Destin on vacation or invest in your new family beach house, there are plenty of ways to experience Holiday Isle for yourself. 

A woman in a gray dress holding a baby on the beach Destin Holiday Isle.

If you’re looking to rent, Holiday Isle Properties Inc. is a great place to start. They can help you find the perfect property for your stay, whether it’s a waterfront resort or a cozy single-family home. Most of their beachfront condos and vacation rentals come with beach service, including two beach chairs and an umbrella that are set up for you at the beginning of the day. 

While there are plenty of places to stay around Destin, there’s truly nowhere like Holiday Isle. 

A family posing for a photo on the beach.

Shopping Around Destin Holiday Isle

Destin Commons

Destin Commons is an upscale shopping center that has become Destin’s most popular designation for fashion, food, and family-friendly experiences. With over 85 stores and restaurants, including some of the most popular retailers in apparel, jewelry, and electronics, it’s the perfect place to shop for anything you need. Destin Commons is also home to a budding collection of interactive murals perfect for Insta-worthy photos. Make it a goal to visit them all! 

A man holding a baby on the beach.

Grand Boulevard

Grand Boulevard is home to a variety of boutiques and national retail brands that are perfect for a day of shopping. With brands like Anthropologie, Kendra Scott, and Vineyard Vines, you can find a treat for yourself or a gift for anyone on your list. Grand Boulevard also offers a variety of exciting events and a weekly farmers market on Saturday mornings. When you need to refuel, visit one of their delicious restaurants for a casual bite or a fine dining experience. 

Harborwalk Village 

Harborwalk Village combines some of the best shopping in Destin with all of the views, excitement, and joy of the nearby water. Whether you’re shopping for souvenirs, apparel, toys, or anything special, you’ll be able to find it at one of Harborwalk Village’s unique retailers. Grab a boardwalk snack like a soft pretzel or a funnel cake, or enjoy some signature seafood at one of their waterfront dining restaurants.

A family on the beach holding a baby.


Amazing Restaurants Around Holiday Isle in Destin

You can’t have a great vacation without great food, which is why there are several fabulous restaurants close to Holiday Isle! While the peninsula itself is primarily residential, all of these restaurants are a short drive or Uber ride from most of the rental properties. Here are a few of my favorite spots for a delicious meal around Holiday Isle! 

A boy in a striped shirt standing on the beach Destin Holiday Isle.

Boshamps Seafood & Oyster House

Located on the gorgeous Destin Harbor, Boshamps is the place to go for spectacular waterfront dining. For almost 30 years, Boshamps, then known as The Flamingo Cafe, was Destin Holiday Isle’s premier white tablecloth restaurant until the family and chef began dreaming about what could be if they stripped away some of the formality. Today, Boshamps offers the same quality fine dining menu but with a comfortable, casual, and family-friendly atmosphere. Their menu features plenty of local seafood and some specialty cocktails that are perfect for sipping while looking out over the water. 

Louisiana Lagniappe

Louisiana Lagniappe has been serving upscale Gulf seafood with a Creole flair for over 30 years and has become a beloved restaurant that keeps guests returning again and again. Located inside the Sandpiper Cove condominiums, they provide an upscale waterfront dining experience for the entire family year-round. They are consistently ranked in the Top 10 restaurants on TripAdvisor, and they win the Award of Excellence year after year.

A family poses for a family photo on the beach.

Dewey Destin’s Harborside Restaurant

Dewey’s great-great-grandfather was Leonard Destin, who founded the town back in 1835, and today, Dewey’s restaurant celebrates the legacy of Leonard’s early discovery. Dewey Destin’s Harborside Restaurant serves fresh, sustainable seafood in Old Florida. While their fish, shrimp, and oysters are out of this world, they’re also known for their steaks, salads, and other delicious menu items.  

A couple dances on the beach holding hands at Destin Holiday Isle.

Brotula’s Seafood House & Steamer

Brotula’s was named after the Bearded Brotula, or Cusk Eel, caught right in the local waters near the restaurant and considered to be one of the best-kept secrets in the local fishing community. Their restaurant specializes in fresh, locally sourced seafood and produce and is known for its steamed and boiled shellfish platters. A little more on the casual side, Brotula’s is still a waterfront dining experience that will make you feel like you’re truly on vacation. 

A young boy in a white shirt standing on the beach Destin Holiday Isle.


A little further out but well worth the drive is Bijou, a fine dining restaurant that embodies “coastal cuisine with a New Orleans flair.” Their menu features the freshest Gulf seafood, prime steaks, and an award-winning wine list. The atmosphere is a bit more formal than other area restaurants, so it’s perfect for a night of giving your flip-flops a good rest. Be sure to stop by their Lounge for one of their specialty martinis! 

Sure, a waterfront seafood dinner is quintessential to a Holiday Isle vacay, but a girl’s gotta eat breakfast, too! Here are some of the best local Destin Holiday Isle spots to grab a bite to eat first thing in the morning before you start another day in paradise. 

A family is playing on the beach with their children Destin Holiday Isle.


Breakfast is the most important meal of the day, and Crackings has some of the best in the area! They use the highest quality ingredients to fuel you for a day at the beach with delicious twists on breakfast classics. Pro tip: it gets busy, so join the Yelp Live waitlist before you arrive!

Blue Mahoe Cafe

Getting its name from the national tree of Jamaica, Blue Mahoe Cafe is the place to go for a hearty, delicious breakfast. Whether you’re looking for classic Southern dishes, omelets, or something to satisfy your sweet tooth, these beautiful breakfasts will appease every palate. Keep your eye out for some delicious Jamaican-inspired dishes, too!

A woman in a gray dress holding a baby on the beach Destin Holiday Isle.

Entertainment Around Destin Holiday Isle

Whether you’re visiting Holiday Isle for a vacation or are a local in need of a new adventure, there is always something to do in Holiday Isle! Sure, a classic day on the beach can’t be beat, but there are plenty of ways to experience everything Holiday Isle has to offer. 

Cruisin’ Tikis Destin

There is no better way to experience the beauty of Destin Holiday Isle than from the water! Cruisin’ Tikis is a fleet of floating Tiki huts that literally cruise the Gulf! You’ll have a certified captain driving, so you’re free to enjoy any beverages (adult or otherwise) that you bring onto the cruise with you! They offer 3 and 4-hour cruises, as well as a 1.5-hour sunset cruise that is as spectacular as it sounds. Kids are welcome, too! 

A boy kicking a ball in the ocean Destin Holiday Isle.

Destin Parasailing

Okay, if there’s any better way to enjoy the beauty of Holiday Isle than from the water, it’s gotta be soaring over it. Destin Parasailing uses the latest in Parasailing technology to ensure that you can safely glide over the water on a fun adventure. Double and triple parasailing rides are available, and if you’re feeling really daring, check out their photo packages available for purchase! 

Destin Dolphin Cruises

It’s an amazing thing to see a dolphin diving and playing in its natural habitat, and we’re lucky that so many dolphins call the Destin Holiday Isle area home! Destin Dolphin Cruises invites you to experience the emerald green waters of the Gulf of Mexico aboard their boat as they sail through some of the dolphins’ most popular hangout spots! You can kick back and relax on the main deck or the upper deck as you keep your eye out for splashing dolphins. Join them on one of their sunset cruises for an even more incredible experience!  

Three boys sitting on the sand with a baby in their arms in Destin Holiday Isle.

Sunquest Cruises

What’s even better than dinner looking out over the water? How about a luxury meal on the water? Sail aboard the Solaris, a 125’ yacht with three decks of indoor and outdoor spaces. Enjoy a drink or two, live music, and a three-course meal as you sail on the water of Destin, taking in some extraordinary views. 

Destin Brewery

If you’re traveling with a Holiday Isle beer-lover, you’ll definitely want to check out Destin Brewery for a laid-back visit and the opportunity to taste some of their award-winning craft beers! While they have some favorites that are on tap year-round, there are always seasonal brews to try, tantalizing your taste buds. Pick up a few cans of your favorite to enjoy on a warm afternoon on the beach! 

A family is playing in the sand on the beach Destin Holiday Isle.

Entertainment Kids Will Love at Holiday Isle in Destin!

Destin is a fantastic family destination, and as such, there are plenty of fun and exciting things to do with your kids! Here are some of the best ways to spend a day in Destin with the whole family. 

A family poses on the beach with their children.

Buccaneer Pirate Cruise

If you’ve got kids who love a little adventure, they’ll love searching for undiscovered treasure aboard the Destin Holiday Isle’s Buccaneer Pirate Cruise! The captain and mates will keep your entire crew entertained with pirate-themed activities, banter, singing, dancing, and other family fun. All sailors will have the opportunity to engage in pirate training, sword fighting, water gun battles, and even authentic cannon fire! Have a blast alongside your kids as they become swashbuckling pirates sailing aboard the seas of Destin. 

A family of five standing on a beach at Destin Holiday Isle

Gator Beach Alligator Park

There are few things more quintessentially Florida than alligators, and Gator Beach Alligator Park allows you to get up close and personal with these incredible creatures. Take the Discovery Tour to learn more about gators and help their team at feeding time, or try out the VIP Gator experience to see how the Gator Beach team cares for their animals on a daily basis, and have your picture taken holding a baby gator! Then, when you’re hungry, check out the attached restaurant, Fudpuckers, a Destin institution with great food, drinks, and events. 

Big Kahuna’s Destin

Big Kahuna’s is the Emerald Coast’s largest water park, packed full of rides, slides, and other thrills! Enjoy awesome water slides or relaxing lazy rivers, staying cool without having to worry about sand. Lay out by one of Big’ Kahuna’s pools and soak up the sun or indulge in a Cabana for a private, shady space. It’s a great alternative to a beach day and with plenty of extra excitement!

Two boys sitting on the beach in front of houses Destin Holiday Isle.

Visit Destin Holiday Isle

Holiday Isle in Destin, Florida, is one of my favorite places in the world, and I know that if you visit for yourself, it will quickly become yours, too. I highly encourage you to rent a condo on the water, enjoy some of the world’s freshest seafood, and take on a new adventure. I promise you’ll fall in love just like I did!

Okay, so you have your vacation planned. Now, it’s time to think about pictures! I’m a Destin family photographer, and I adore working with families so they can have gorgeous memories of these special times. As a mom myself, I know how fast this stage flies by, and I want to help you remember it! If you’ve been looking for a photographer who will be there to help you capture these early years, let’s chat! Contact me today so we can book your session. And for more Destin area content, check out the blog links below.

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