Holiday Isle Real Estate

Holiday Isle Real Estate

Welcome to Holiday Isle, a premier waterfront subdivision located in the heart of Destin, Florida. Nestled in Okaloosa County, Holiday Isle offers the perfect blend of luxurious coastal living and a vibrant community atmosphere.

This exclusive neighborhood boasts stunning waterfront properties, including beachfront estates, canal-front homes, and upscale condominiums. Residents of Holiday Isle enjoy breathtaking views of the Gulf of Mexico and easy access to pristine white sandy beaches.

In addition to its picturesque surroundings, Holiday Isle provides residents with a variety of amenities, including private beach access, marinas for boating enthusiasts, and close proximity to top-rated restaurants and shopping destinations.

Whether you're looking for a permanent residence or a vacation home, Holiday Isle offers the ideal setting for those seeking a waterfront lifestyle in Destin, Florida. Experience the ultimate in coastal living at Holiday Isle, where every day feels like a holiday.

Newest Listings in Holiday Isle

501 Osceola Dr, Destin
$9,900,000
4 Beds ⋅ 6 Baths ⋅ 1014399 MLS
Welcome to life on Destin Harbor, where mornings begin with soft sunlight dancing across the water and evenings settle into the glow of fire pits reflecting off the pool. Nestled on a rare 73-foot harbor frontage lot in Holiday Isle, this brand-new coastal sanctuary is more than a home -- it's a daily invitation to slow down, breathe deeply, and savor the beauty of waterfront living. Every custom detail inside has been thoughtfully crafted to elevate comfort and connection. Shell stone flooring carries you through warm, light filled spaces, while designer lighting sets the tone for both lively gatherings and quiet moments. The heart of the home is a stunning chef's kitchen with two islands, Venetian plaster ceiling detail, motorized cabinetry, and a wraparound pantry -- a space designed for cooking, hosting, and lingering with friends. Wet bars on both levels make entertaining effortless, whether you're serving morning coffee or sunset cocktails. The second-floor primary suite feels like a private retreat, complete with a spa inspired bath featuring custom acrylic cabinetry, double vanities, a soaking tub, and a walk-in shower with four shower heads. Additional ensuite guest rooms and a spacious bunk room ensure everyone has a place to unwind. A dedicated office and multi-functional bonus room offer flexibility for work, creativity, or play. Step outside and the lifestyle expands. Two generous harbor front terraces overlook boats gliding by, dolphins passing through, and the sparkling lights of Destin's waterfront. The large private pool -- framed by fire features and a calming water element -- becomes the centerpiece for unforgettable days and nights spent outdoors. With an elevator, climate-controlled garage spaces, whole house generator, impact rated windows and doors, and smart home technology throughout, this residence blends luxury with peace of mind. Concrete block construction and a metal roof add strength and longevity, while thoughtful touches like surround sound, keyless entry, and smart water leak detection enhance everyday ease. Beyond the dock and harbor views, the best of Destin is right at your doorstep. Just a short walk or bike ride away, you'll find some of the area's most beautiful public beach accesses, making spontaneous mornings on the sugar-white sand and emerald waters part of everyday life. For boating enthusiasts, waterfront dining, entertainment, and adventure are only moments away. Cruise by private boat or hop aboard a water taxi to waterfront restaurants, harbor attractions, and the famous Crab Island sandbar for a day on the water. Anglers will appreciate that this location is truly a fisherman's paradise, with world-class deep-sea fishing opportunities just minutes from the Destin Pass and the convenience of casting a line right from your own private dock. Whether you're heading offshore for a day of fishing, boating to dinner at sunset, relaxing at Crab Island, or enjoying a quick ride to the beach, this exceptional location offers the rare opportunity to experience the very best of both harbor-front and beachside living. 501 Osceola Drive is a home built for gathering, relaxing, and celebrating life on the water -- a rare opportunity to live beautifully on Destin Harbor.

501 Osceola Dr, Destin
105 Durango Rd, Destin
$995,000
3 Beds ⋅ 3 Baths ⋅ 1012816 MLS
Life on the harbor takes center stage at this renovated waterfront townhome, where a deeded 40-foot boat slip with lift places days on the water just steps from home. Set along the protected canals of Destin Harbor with nearby private beach access, the turnkey residence offers an exceptional setting for those who want boating, beach days and refined coastal living within easy reach. Spanning 1,558 square feet across two thoughtfully designed levels, the three-bedroom, three-bath custom townhome has been meticulously updated throughout. Vaulted ceilings and exposed beam detailing bring architectural character to the bright, open living and dining areas, while hardwood and tile flooring, custom furnishings and curated coastal décor create a polished yet relaxed atmosphere. The renovated kitchen is designed for everyday living and entertaining, with stainless steel appliances, ample cabinetry, a generous breakfast bar, and modern lighting. Its open connection to the dining and living areas keeps the waterfront lifestyle at the heart of the home. Two levels of outdoor living extend the residence toward the harbor. A covered water-level patio provides a shaded retreat just steps from the private boat slip, while an expansive upper deck with a built-in grill station offers generous space for alfresco dining, entertaining and enjoying the harbor breeze. The first-floor primary suite features direct access to the outdoor living area, a custom closet system and an updated bath with a soaking tub, glass-enclosed shower and designer tile work. A split-bedroom floor plan provides privacy for family and guests, with two additional bedrooms and two full baths completing the layout. With direct water access, a deeded 40-foot boat slip with lift, private beach access and a comprehensive renovation, this harborfront residence offers an amazing opportunity for full-time waterfront living or a sophisticated coastal retreat centered around life on the water.

105 Durango Rd, Destin
109 Durango Rd, Destin
$929,000
3 Beds ⋅ 3 Baths ⋅ 1011521 MLS
Boat or beach - you don't have to choose. Set waterfront along the protected canals of the Destin Harbor, 109 Durango Road pairs a private boat slip with a 20,000-lb boat lift, currently accommodating a 35-foot boat, and walking distance to Holiday Isle's private beach access. Completely transformed by a local design team, this three-bedroom, three-bath waterfront townhome feels less like a typical townhouse and more like a curated coastal retreat designed around life on the water. Custom white oak cabinetry and millwork, Venetian plaster, Italian and Moroccan tile, quartz surfaces, designer lighting and fixtures, and rich Ipe decking create an elevated finish rarely found in this location at this price point. The first-floor primary king suite opens to a private waterfront terrace just steps from the boat slip and features a spa-like bath with jetted tub and separate shower. Custom white oak barn doors and fitted built-ins continue throughout all closets in the home, while an additional king suite with ensuite bath completes the first level. Upstairs, the home opens dramatically into a light-filled living, kitchen and dining space with wide-open sightlines and an unexpectedly generous sense of scale. The kitchen is anchored by mitered-edge waterfall quartz countertops, custom-milled white oak cabinetry and a striking marble backsplash, while Venetian plaster adds another layer of texture and refinement. A wall of glass doors extend the living space onto an expansive waterfront terrace that feels like a destination of its own. Multiple conversation and lounge areas create room for entertaining or unwinding, while a full summer kitchen with quartz countertops, built-in grill and refrigerator makes outdoor living effortless. Sleek glass railings preserve the open water views and reinforce the modern coastal aesthetic found throughout the residence. A flexible third bedroom adds a custom queen Murphy bed surrounded by built-in shelving and drawers, allowing the space to transition easily between guest accommodations and additional living space. But perhaps the greatest luxury here is how effortlessly the water becomes part of everyday life. Start the morning with coffee and a quiet cruise through the Destin Harbor. Spend the afternoon anchored at Crab Island, head offshore through East Pass for a day of Gulf fishing, or leave the boat behind and make the short trip to the beach. As the day winds down, take the boat out for a sunset cruise, pour a glass of wine and watch the harbor lights come alive. Few Destin waterfront properties bring together this level of design, private boating access and proximity to a private beach. A special harbor deserves a special residence. This is waterfront Destin living reimagined.

109 Durango Rd, Destin
514 Vera Cruz Dr, Destin
$2,599,000
6 Beds ⋅ 6 Baths ⋅ 1010454 MLS
Experience the ultimate Destin lifestyle from this exceptional canal-front beach home in the highly desirable community of Holiday Isle. Spend your mornings enjoying Gulf views, or boating to Crab Island and your evenings relaxing after a day on the water. The property offers 90 ft of deep-water canal frontage and two covered boat slips with lifts, making it easy to enjoy everything Destin's boating lifestyle has to offer. Designed for effortless coastal living, the home features a fully covered and enclosed outdoor entertainment area ideal for gathering with family and friends and enjoying coastal breezes. The property includes two separate living spaces: the second-level main residence and a third-level lockout. Each has its own private entrance and can be enjoyed together or independently, offering flexibility for extended family, guests or vacation-rental opportunities. The main residence features four spacious bedrooms, four full bathrooms, an expansive living area, a gourmet kitchen with breakfast bar and a private office. The third-level lockout offers two additional bedrooms, two full bathrooms, a large living area and fully equipped kitchen with breakfast bar. The lower-level space offers room for storing beach gear, paddleboards, fishing gear and boating supplies, workshop. The private beach access is a very short walk away, while Crab Island and Gulf of Mexico are 15 minutes away by boat. This one-of-a-kind property captures the very best of the Destin lifestyle!

514 Vera Cruz Dr, Destin
521 Gulf Shore Dr, Destin
$1,750,000
5 Beds ⋅ 3 Baths ⋅ 1009704 MLS
Open House! Friday, Oct 30th from 3pm-6pm. Welcome to Holiday Isle! This 5-bedroom, 3-bath waterfront home comfortably sleeps 14 guests and offers an incredible opportunity as a primary residence, second home, or established vacation rental. The spacious open-concept living area is designed for entertaining and opens to one of the largest waterfront decks on Holiday Isle, providing plenty of room for outdoor dining, gatherings, and enjoying the water views. The deck has even been used to host weddings, offering endless possibilities for entertaining. Boating enthusiasts will appreciate the private dock with two boat lifts and a dedicated fish cleaning station. Cruise to Crab Island, spend the day fishing in the World's Luckiest Fishing Village, or explore Destin's waterways right from your backyard. The home also features a large second-floor front balcony, perfect for morning coffee or relaxing in the evening after a day on the water. Located just across the street from the Gulf of America, you'll enjoy a short walk to the private gated beach access where you can spend the day on Destin's sugar-white sand and emerald waters. With spacious accommodations, exceptional outdoor living, premier boating amenities, and an unbeatable Holiday Isle location, this property offers outstanding rental potential and the coastal lifestyle buyers are looking for.

521 Gulf Shore Dr, Destin
604 Magnolia Dr, Destin
$1,855,000
4 Beds ⋅ 4 Baths ⋅ 1009415 MLS
Discover this charming 4 bedroom/ 3.5 bath Florida beach-style cottage nestled in the beautiful neighborhood of Holiday Isle. This property boasts not only a private pool, but also an impressive 90 feet of dock space, perfect for boating enthusiasts. It is a short walk to the pristine white sands and Emerald waters of the Holiday Isle private beaches. Enjoy entertaining on the second level with an open floor plan, the kitchen opens to the large living room space. The second level features a separate formal dining room with french doors that opens to the wrap around balconies. This home features a master bedroom on the third level with an office and a private sunroom to enjoy gulf views.The survey is located under the Documents Tab. Inquire for more information and to schedule a showing

604 Magnolia Dr, Destin
129 Durango Rd Unit 1, Destin
$1,084,000
3 Beds ⋅ 3 Baths ⋅ 1007735 MLS
Waterfront living meets beach lifestyle in this beautifully remodeled townhome featuring a covered boat lift and private beach access just a short walk away. Perfectly positioned on a wide canal, you'll enjoy easy boating with quick access to Destin Pass, the Gulf of Mexico, and Crab Island in under 15 minutes by boat. Designed for entertaining, the expansive waterfront deck offers plenty of space to relax, dine, or unwind by the fire pit while enjoying sunrise views. A hot tub, covered lanai, and private dock create the ultimate outdoor retreat. Inside, the home has been thoughtfully updated with a custom kitchen featuring an 8-foot butcher block island, granite countertops, stainless steel appliances, and a spacious pantry. The lower level includes a custom wet bar with wine cooler, beverage cooler, and live-edge cypress countertop, plus a second living area that could easily serve as a game room to maximize vacation rental appeal. Additional highlights include a fenced maintenance-free side yard, and room to enjoy kayaking, paddle boarding, fishing, or simply stepping onto your boat from your backyard. Offered furnished, this is a rare opportunity to own a turnkey waterfront property that combines boating, beach access, and exceptional outdoor living in the heart of Destin.

129 Durango Rd Unit 1, Destin
522 Osceola Dr, Destin
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 1005035 MLS
Welcome to the best of both worlds with the beach and boating lifestyle located on Holiday Isle. This fully renovated, 4-bedroom, 3-bathroom coastal retreat is just two blocks from the beach and sits on a deep-water canal, offering the perfect waterfront lifestyle. With spacious living areas on both levels. Stylish finishes, modern appliances, and expansive outdoor spaces create a welcoming atmosphere for relaxing or entertaining. Enjoy beach living, boat access, and luxurious comfort all in one stunning property. Ideal for vacation rentals or personal use!

522 Osceola Dr, Destin
609 Lagoon Dr, Destin
$7,850,000
4 Beds ⋅ 5 Baths ⋅ 999201 MLS
Welcome to 609 Lagoon Drive, a yachtsman's dream, this harbor-front luxury legacy home offers an exceptional opportunity to own on prestigious Holiday Isle.Positioned on deep water with a private boat slip accommodating a 70+ foot yacht, this property encompasses 90 feet of waterfront footage ideal for those who embrace the boating and fishing lifestyle. For the beach enthusiast you are a quick 5 minute walk or short golf cart ride to the beautiful, pristine, white sand beaches. Spanning 5,192 square feet, this estate has been cherished as a family vacation home for almost two decades, designed for gathering, entertaining, and creating lasting memories. This home boasts beautiful hand selected white pine floors throughout, exposed hand hewn beams, chefs kitchen with commercial grade appliances, custom cabinetry and stunning harbor views from every floor. The master suite situated on the third floor offers his and hers walk in cedar closets, separate vanities, garden tub and a walk in shower. The french doors off of the master suite open directly to the luxurious covered balcony with panoramic views of the Destin Harbor to enjoy the beautiful sunsets over the water. A private study with fireplace directly off of the master suite and an elevator are just a few of the many amazing details that encompass 609 Lagoon Drive. Enjoy the convenience of the Destin Water Taxi right off your dock for evenings out, and waterside dining. Contact Catherine Williams to find out more details or for a private showing. Buyer to verify all dimensions

609 Lagoon Dr, Destin
517 Osceola Dr, Destin
$1,875,000
3 Beds ⋅ 3 Baths ⋅ 998328 MLS
Waterfront luxury meets effortless coastal living--this is the Emerald Coast dream, fully realized. 90 feet of prime waterfront, private boat slips, jet ski lifts, a resort-style pool, and deeded beach access within a short bike or golf cart ride. This is where boating days, beach sunsets, and effortless entertaining become your everyday reality. Launch from your private dock and be at Crab Island or in the Gulf in under 10 minutes. Whether it's boating, fishing, or dock-to-dinner nights via water taxi, this location delivers the ultimate coastal lifestyle. Offered turnkey and fully furnished, this home is ready to generate income or unforgettable memories from day one.Start your mornings with coffee and sunrise views from expansive wraparound balconies. Spend your days entertaining by the heated pool and spa, grilling on the deck, or unwinding fireside while casting a line from your private dockFirst level features two large garages, a bedroom, full bath, laundry, and a massive bonus space perfect for a game room, bunk room, or office. Second level showcases two spacious waterfront primary suites, each with private balcony access, en-suite baths, and walk-in closets The heart of the home is a generous open-concept kitchen and living area centered around a cozy fireplace--ideal for gathering after a day on the water. Whether you're building your investment portfolio, searching for a second home, or ready for full-time coastal living,The only thing missing is you. Schedule your private viewing now and experience it firsthand.

517 Osceola Dr, Destin
524 Vera Cruz Dr, Destin
$2,245,000
4 Beds ⋅ 2 Baths ⋅ 997269 MLS
This spacious waterfront home enjoys a stunning location right on a deepwater mooring with two boat lifts and easy access to the harbor and gulf. Even when you're not out on the water, the private pool and hot tub provide canal views while the party-sized observation deck is the ultimate place to view seasonal fireworks and breathtaking sunsets. Inside, the home continues to maximize those waterfront views with an open concept living space and chef's kitchen finished to a high standard of luxury. Gleaming tile floors flow through each beautifully furnished space while the cathedral ceiling provides a sense of airy spaciousness.

524 Vera Cruz Dr, Destin
621 Choctaw Dr, Destin
$2,299,000
4 Beds ⋅ 5 Baths ⋅ 997240 MLS
Located in the highly sought-after Holiday Isle area of Destin, this beautifu 4-bedroom, 4-bath waterfront home offers the perfect blend of coastal living and boating convenience. Just two blocks from the white sandy beaches of the Gulf of Mexico, this property provides easy beach access while enjoying the privacy and exclusivity of Holiday Isle. Designed with boaters in mind, the property features two covered boat slips and a 50-foot dock, providing ample space to accommodate a large vessel and additional watercraft. Also features a new seawall. With direct water access, it is ideal for boating, fishing, or simply enjoying life on the water. The home offers four spacious bedrooms and four full bathrooms, providing comfortable accommodations for family and guests. A private pool creates the perfect outdoor retreat for relaxing or entertaining after a day on the water or at the beach. The property has been recently painted, giving it a fresh and well-maintained appearance. Whether you are searching for a primary residence, second home, or investment opportunity, this exceptional Holiday Isle property combines a prime Destin location with desirable waterfront amenities and close proximity to the beach.

621 Choctaw Dr, Destin
Start Your Search

Vendor Member Number : 28166

How much is your home worth?

Get instant property value now!