Holiday Isle, FL Real Estate Search

Holiday Isle, FL Single Family Homes for Sale

Holiday Isle, FL, is a picturesque locale that offers an enticing array of single-family homes for sale, catering to both investors and families seeking a vibrant coastal lifestyle. Nestled between the emerald waters of the Gulf of Mexico and the serene view of Destin Harbor, this area is renowned for its beautiful beaches and charming neighborhoods. Properties here often feature spacious layouts, modern amenities, and outdoor spaces perfect for entertaining or relaxing in the sun. With its close proximity to recreational activities, dining, and shopping, Holiday Isle presents an appealing opportunity for homeowners looking to immerse themselves in a thriving community while enjoying the natural beauty of Florida's coastline.

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Newest Holiday Isle, FL Single Family Homes for Sale

501 Osceola Dr, Destin
$9,900,000
4 Beds ⋅ 6 Baths ⋅ 1014399 MLS ⋅ 5,795 SqFt.
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
514 Vera Cruz Dr, Destin
$2,599,000
6 Beds ⋅ 6 Baths ⋅ 1010454 MLS ⋅ 3,750 SqFt.
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 Drive, Destin
$1,875,000
5 Beds ⋅ 3 Baths ⋅ 793884 MLS
OPEN HOUSE! SATURDAY AUG. 29th from 2PM to 4:30PM, SUNDAY, AUG. 30TH from 10-12:30pm. 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 Drive, Destin
521 Gulf Shore Dr, Destin
$1,750,000
5 Beds ⋅ 3 Baths ⋅ 1009704 MLS ⋅ 3,276 SqFt.
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 ⋅ 3,474 SqFt.
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
522 Osceola Dr, Destin
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 1005035 MLS ⋅ 2,396 SqFt.
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 ⋅ 5,192 SqFt.
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 ⋅ 2,308 SqFt.
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 ⋅ 2,166 SqFt.
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 ⋅ 3,231 SqFt.
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
24 Norriego Rd, Destin
$3,950,000
5 Beds ⋅ 6 Baths ⋅ 914155 MLS ⋅ 5,081 SqFt.
Welcome to 24 Norriego Road of the prestigious Holiday Isle waterfront community in Destin, Florida! This trophy property, a yachtsman's deep-water dream estate, was constructed new in 2014 and contains 5,000+ square foot of meticulous design and craftsmanship, 5 bedrooms with ensuite bathrooms, an elevator, a powder room serving guests located between the expansive kitchen and primary living room, and a full bath on the first floor adjacent to an area that could be flexible for the addition of an additional bedroom, bunk room, secondary media room, and/or game room, all oriented on a superior lot that offers sensational view corridors to the scenic bodies of water that surround this exclusive family compound. Spaciousness throughout the home, including the oversized garages, will.. comfortably and privately accommodate extended family to enjoy the irreplaceable lifestyle this property offers. There is such uniqueness of enjoying this spectacular estate and its private, waterfront pool, then boating to 'Crab Island', or perhaps the sensational fishing offshore in the Gulf of Mexico only minutes away from the oversized, deep-water dock, currently fitted with a 20,000lb boat lift; meanwhile others in your family can enjoy exclusive community beach access to one of the world's greatest beaches within approximately 1000' of this home's front door, which also accommodates golf carts. The finishes and features throughout are extraordinary, as the owner spared no expense whatsoever. Please inquire for further details and to schedule your private showing.

24 Norriego Rd, Destin
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