Holiday Heights Real Estate

Holiday Heights Real Estate

Welcome to Holiday Heights, a captivating development nestled in the heart of Fort Myers Beach, Florida. This charming community is a true gem in Lee County, perfectly blending the allure of coastal living with the comforts of modern amenities.

Holiday Heights offers an idyllic lifestyle characterized by sun-kissed beaches, swaying palm trees, and stunning sunsets that paint the sky in vibrant hues. Imagine waking up to the gentle sounds of the ocean and enjoying your morning coffee on a spacious balcony, soaking in the serene surroundings. Each thoughtfully designed residence within Holiday Heights features open floor plans, contemporary finishes, and an abundance of natural light, ensuring a warm and inviting atmosphere for you and your loved ones.

Beyond the beautiful homes, Holiday Heights is strategically located just moments away from the pristine shores of Fort Myers Beach, where you can indulge in a variety of outdoor activities, from sunbathing and swimming to water sports and fishing. The nearby bustling Times Square offers an array of dining, shopping, and entertainment options, making it easy to savor the vibrant local culture.

For those who appreciate nature, the area is rich with parks and preserves, perfect for hiking, biking, or simply enjoying the beauty of Florida's unique ecosystems. Whether you’re looking for a permanent residence, a vacation getaway, or an investment opportunity, Holiday Heights promises a lifestyle of relaxation, adventure, and community.

Discover your dream home at Holiday Heights, where every day feels like a vacation!

Newest Listings in Holiday Heights

$1,674,500
226025588 MLS
PREMIER BAYFRONT HOMESITE — BUILD YOUR DREAM HOME ON ESTERO BAY Paradise awaits on this rare, oversized Bayfront homesite offering direct Gulf access along the protected and prestigious Estero Bay Aquatic Preserve. Spanning 11,230 square feet with an impressive 95 feet of Bay frontage and 155 feet of depth, this exceptional property provides the ideal canvas to construct a new elevated two- or three-story Bayfront residence designed to capture sweeping water views and unforgettable sunsets. Enjoy front-row seating to nature’s daily show—dolphins and manatees gliding through the bay—right from your future private dock. Positioned on a quiet cul-de-sac and among the highest elevations on the island, this property is located within the highly desirable Holiday Heights neighborhood, offering both privacy and prestige. The existing structure is considered a teardown, and the property is being sold at lot value, allowing full creative freedom to design a custom home perfectly tailored to your lifestyle. Multiple builder introductions are available to assist in bringing your vision to life. Just a short stroll to deeded beach access, a nearby marina, and a grocery store, this one-of-a-kind bayfront parcel delivers the ultimate blend of boating, beach, and luxury island living. This is a rare opportunity to create a true coastal residence and be part of the ongoing Fort Myers Beach Renaissance.

5630 Williams Drive, Fort Myers Beach
$845,000
3 Beds ⋅ 2 Baths ⋅ 226019397 MLS
Newer construction built in 2023! Potential Income Producer. This Elevated Florida-Style Fully Furnished Turnkey Beach Home offers the rare combination of luxury living for a lifetime of Cherished Memories and provides potential Income in Weekly Zone that you need. Exceptional Rental History, highly rated on popular 3rd party rental sites. Close to the beach, Shopping and Dining. Absentee Ownership Made Easy. Room pool or Swim spa. Whether you want a personal Island Escape, a Second Home, or an Income Producing Investment Property, this home delivers lifestyle and revenue.

431 Lazy Way, Fort Myers Beach
$2,500,000
3 Beds ⋅ 2 Baths ⋅ 2026012584 MLS
Newly built elevated gulf access pool home located in the desirable Holiday Heights neighborhood on Fort Myers Beach. Completed in 2025 and gently used since, this 3 bedroom 2 bathroom home offers a coastal feel with quality design and beautiful finishes. You may ascend to the living area using 1 of 2 composite staircases or call for your private elevator to transport you up to the property. Once inside you will admire the great room, teeming with natural light through the impact windows, complete with formal dining for 10, a comfy yet sophisticated living room, and sensational kitchen outfitted with stainless steel appliances, marble island, wine fridge, and 4-person breakfast bar. The spacious primary bedroom, with pocket sliders leading out to the deck and ensuite bathroom, provides a quiet sanctuary for the owners. You will find 2 guest bedrooms separated by a beautifully appointed bathroom on the other side of the home, perfect for families or guests. Once back downstairs and outside you can enjoy a large heated saltwater pool with sun shelf overlooking the canal with views of the bay. When you are ready to hit the water, the newly constructed dock with electric boat lift is the perfect spot to store your vessel. This beach property is located just minutes from Publix , shopping and dining options of Santini Plaza, and the Margaritaville Resort.

5545 Avenida Pescadora, Fort Myers Beach
$4,900,000
5 Beds ⋅ 5 Baths ⋅ 226012044 MLS
Luxury Bayfront Estate | Expansive Bay Views & Resort-Style Living! Imagine waking up each morning to panoramic 180° Bay Views, where the sun rises gracefully over the bay and sets in a blaze of color on the horizon. 30,000 lb Synergy Boatlift, 5 ensuites, elevator, 3+ car garage. Nearly every room in this home captures breathtaking views, immersing you in the beauty of coastal living. After sunset, retreat to the dock, the lanai, or your private master deck to watch the stars emerge—on a clear night, hundreds sparkle above, and you may even glimpse rockets launching from Cape Canaveral. The soothing sound of the distant ocean waves completes the picture of tranquility. The newly remodeled heated saltwater pool and spa create your own private resort. Relax with music or a favorite show on the lanai’s large-screen TV, or gather for a cozy movie night under the stars. With five spacious en-suite bedrooms, the home provides ultimate privacy and comfort for family and guests alike. The open-concept kitchen and dining areas accommodate up to 14, making it perfect for entertaining on any scale. Every detail of this residence is designed for both luxury and function. A 3+ car garage with a newly finished multi-coat polyurea floor offers abundant storage, while numerous large closets ensure everything has its place. Beyond the home, the lush landscape is adorned with fragrant flowering plants and stately palms, creating a true tropical retreat. For the boating enthusiast, the private dock system is unparalleled. Outfitted with a 30,000 lb. Synergy boat lift and new boathouse roof, a double IMM Quality PWC lift and 50-amp shore power, it has been fully re-decked with premium AZEK materials for durability and style. Launch your kayak or paddleboard from the floating EZ Dock and explore mangrove islands teeming with dolphins, manatees, stingrays, & native birds—even the occasional bald eagle. Quick Gulf access means you can reach Big Carlos Pass in about 12 minutes, enjoy a trip to Naples or Marco Island in just over an hour, or head north for a scenic ride to Cabbage Key. At home, cast a line off the dock for snapper or sheepshead while enjoying the evening migration of ibis or the sight of dolphins gliding by. This smartly equipped residence ensures modern comfort with high-speed mesh Wi-Fi extending throughout the home, pool deck, and dock. Even while aboard your boat, you can stream video seamlessly. Smart Leviton lighting controls, newer appliances—including GE Profile washer/dryer, KitchenAid dishwasher, and microwave/convection combo—and thoughtfully included furnishings (7 TVs and more) make this property move-in ready. With deeded neighborhood beach access just a 15-minute stroll away, you’ll also enjoy daily sunset gatherings with neighbors on the white sands of the Gulf. This home is more than a residence—it’s an experience of refined coastal living, where every sunrise, sunset, and starry night is yours to savor.

5640 Williams Drive, Fort Myers Beach
$2,299,000
3 Beds ⋅ 3 Baths ⋅ 225074176 MLS
Coastal Waterfront Retreat with Panoramic Estero Bay Views & Gulf Access! Delightfully decorated in a breezy coastal theme, this exceptional 3-bedroom, 3-bath waterfront home offers the ultimate blend of luxury, comfort, and coastal charm. Perfectly situated at the end of a quiet cul-de-sac, this rare property spans nearly ½ acre (.49 acres) and showcases approximately 300 feet of wraparound waterfront along Estero Bay and a scenic intersecting side canal — creating a truly breathtaking backdrop from sunrise to sunset. Beautifully remodeled in 2023, this residence shines inside and out with thoughtful upgrades and high-end finishes. A new metal roof and impact-resistant doors and windows provide lasting peace of mind, energy efficiency, and storm protection. The light-filled interior features an open-concept design that captures sweeping bay views from nearly every room, inviting you to relax and embrace the laid-back Florida lifestyle. Step outside to your private tropical oasis — complete with a heated pool and spa, surrounded by lush landscaping and unobstructed water views. For boating enthusiasts, 2 covered boat lifts (16,000 and 18,000 lb.) and jet ski lifts make it effortless to explore the open water, while a short 10-minute ride to the Gulf of America opens endless opportunities for deep-sea fishing, island hopping, or sunset cruising. Enjoy your morning coffee on the observation pier, cast a line in your backyard, or simply unwind poolside as dolphins and seabirds drift by. The home’s 2-car deep garage offers ample storage and parking for vehicles, golf carts, or beach gear. Inside, you’ll find stylish finishes, and modern lighting that seamlessly blend functionality with coastal elegance. Every detail has been considered — from the smart layout to the thoughtful updates that make this home truly move-in ready. Location is everything, and this one checks every box. You’re just a short stroll to the white sugar-sand beaches, and close to some of the area’s most exciting destinations — including Jimmy Buffett’s Margaritaville Resort, Santini Plaza, Publix, and the newly developed downtown entertainment and dining district. Whether you’re in the mood for live music, fine dining, or boutique shopping, it’s all just minutes away. This home offers something for everyone — boating, fishing, entertaining, or simply soaking in the stunning views. It’s a rare opportunity to own nearly half an acre of prime waterfront in one of Southwest Florida’s most desirable areas. Experience the magic of Estero Bay and the Gulf of America lifestyle — schedule your private showing today!

5596 Avenida Pescadora, Fort Myers Beach
$1,795,000
2025015172 MLS
**PRICE IMPROVEMENT OF NEARLY $150,000!** STUNNING & EXPANSIVE unobstructed BAY & WATERFRONT VIEWS across Estero Bay Aquatic Preserve from this OVERSIZED cleared and buildable BAY FRONT lot! Over 100' of spectacular water frontage on over 1/3 of an acre which wakes up to beautiful sunrises across the bay and is only a short distance to Deeded Beach Access & sunsets on the Gulf! ONE OF THE MOST SOUGHT-AFTER WATERFRONT AND BOATING COMMUNITIES ON THE ISLAND, Holiday Heights, is KNOWN FOR ITS HIGHER ELEVATION AND GULF-ACCESS CANALS and warm & friendly community. Build your custom designed dream home on this oversized bay front lot offering awe inspiring views and the best in coastal living! Located mid-island close to Publix grocery store, trolley stop, full service marina, Fresh Catch Exquisite Waterfront Dining & Junkanoo Below Deck for the more casual waterfront dining experience. Don't miss out on this opportunity to own one of the few vacant bay front lots in this desirable mid island neighborhood location!

5636 Williams Drive, Fort Myers Beach
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