Holiday Heights Homes with Boating Community Type

Welcome to Holiday Heights, a hidden gem in the heart of Fort Myers Beach, Florida! Nestled in Lee County, this vibrant neighborhood offers a unique blend of coastal charm and a welcoming community atmosphere that makes it a perfect place to call home.

Holiday Heights is renowned for its picturesque waterfront properties, where residents can enjoy the luxury of a boating lifestyle. With direct access to the beautiful Gulf of Mexico, this boating community is a haven for water enthusiasts. Whether you’re an avid sailor, a fishing aficionado, or simply enjoy sunset cruises, your dreams can become a reality right from your own backyard.

The neighborhood boasts a variety of homes, each with its own character and charm. From cozy single-family homes to more expansive waterfront estates, there’s something to suit every taste and budget. Many properties come equipped with private docks, allowing for easy access to the water and making it simple to embark on your next aquatic adventure.

Beyond the stunning homes and boating opportunities, Holiday Heights is also conveniently located near a host of amenities. Enjoy the nearby pristine beaches, local parks, and vibrant dining options that Fort Myers Beach has to offer. The community is known for its friendly atmosphere, with neighbors often coming together for social events and gatherings.

In Holiday Heights, you’ll find not just a home, but a lifestyle. Embrace the joys of coastal living and make this enchanting neighborhood your own!

Newest Holiday Heights Homes with Boating Community Type

$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 DR, 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 ⋅ 4.5 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 DR, 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 DR, Fort Myers Beach

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.