A Local’s Guide to the Best Beaches in Islamorada, FL

Nestled in the middle of the Florida Keys, Islamorada is often referred to as the “Village of Islands”—and for good reason. This laid-back stretch of paradise is composed of six beautiful islands that serve as a haven for beach lovers, anglers, and sunseekers alike. While Islamorada may be best known for its world-class sportfishing, it also boasts a stunning variety of beaches that are perfect for relaxing, exploring, or soaking in a quintessential Keys sunset.

Whether planning a weekend getaway, relocating, or just looking for a new spot to unwind, this local guide covers the best beaches in Islamorada—from serene hidden gems to activity-filled hot spots. Plus, if you're considering making this slice of paradise your permanent home, we’ll show you how Pine River Realty can help make that dream a reality.

Anne’s Beach is one of Islamorada’s most beloved and accessible public beaches. Located at Mile Marker 73.5 on Lower Matecumbe Key, this beach is named in honor of local environmentalist Anne Eaton. Unlike traditional sandy shorelines, Anne’s Beach is known for its shallow, warm waters and boardwalk that meanders through mangroves and native vegetation. It’s perfect for a relaxed wade in the water, a casual picnic, or a scenic nature walk.

There are shaded picnic tables, restroom facilities, and multiple entry points to the beach, making it a convenient and peaceful place for families or couples to enjoy an afternoon under the sun. The gentle slope of the shoreline also makes it an ideal spot for kids to play safely in the water.

Tucked behind the Islamorada Public Library on Upper Matecumbe Key, Library Beach Park is a hidden treasure that only locals typically know about. Despite its small size, the beach is charming, intimate, and rarely crowded. A short nature trail leads visitors through lush vegetation to a quiet cove perfect for paddleboarding, kayaking, or a simple beach day.

There’s also a small playground for children, picnic tables for lunch breaks, and plenty of shade provided by native trees. It’s an excellent spot for those looking to avoid the tourist crowds while enjoying a slice of Islamorada’s natural beauty.

Founders Park, located at Mile Marker 87, is one of the most well-maintained public recreational spaces in the Upper Keys. This beach is part of a larger community park that includes an Olympic-size swimming pool, tennis courts, a skate park, and a marina. While there is a small entrance fee for non-residents, the amenities and beach experience are well worth it.

The beach itself offers pristine white sand, calm waters, and ample shade, making it perfect for families and group outings. You can rent kayaks or paddleboards, go snorkeling near the shore, or simply unwind under a palm tree with a good book. The park often hosts community events and live music, adding a festive atmosphere to your beach day.

Part of the popular Postcard Inn Beach Resort and Marina, Holiday Isle Beach offers a more lively and social beach scene. While some parts are reserved for hotel guests, there are areas that are open to the public, especially if you’re visiting one of the on-site restaurants or beach bars.

This beach is ideal for those who want to combine their sunbathing with socializing. Enjoy tropical cocktails, live music, beach volleyball, and watersport rentals all in one place. If you’re in the mood for a more energetic beach day or looking to meet other travelers and locals, Holiday Isle is the place to be.

For the adventurous beachgoer, Indian Key offers a unique experience just offshore from Islamorada. Accessible only by kayak or boat, this island is part of the Florida State Park system and features both historical ruins and pristine coastline. It was once a bustling 19th-century town and is now a ghostly, fascinating relic surrounded by crystal-clear water.

While there isn’t a traditional beach setup with lounge chairs or food vendors, the seclusion and natural surroundings more than make up for it. Pack a lunch, paddle out, and explore the island's ruins before diving into the water for a swim or snorkel among marine life. It’s a perfect combination of history and untouched beauty for those seeking a more immersive experience.

While technically just south of Islamorada, Long Key State Park deserves mention for its tranquil beaches and excellent nature trails. Located at Mile Marker 67.5, this park features mangrove-lined shores, serene campsites, and excellent kayaking and birdwatching opportunities.

The beach here is quiet and perfect for those who want to escape the bustle of busier public spaces. Bring your snorkeling gear or rent a kayak to explore the offshore reefs and seagrass beds, which are home to a variety of marine life. Nature lovers will find Long Key State Park a peaceful retreat just minutes from central Islamorada.

• Bring water shoes: Many of the beaches have rocky or coral-studded bottoms, so water shoes can enhance comfort and safety.
  
  
• Pack reef-safe sunscreen: Help preserve the Keys' delicate marine ecosystems by choosing environmentally friendly sun protection.
  
  
• Respect nature: Avoid disturbing wildlife and take all trash with you. The Keys are home to many protected species, including sea turtles and nesting birds.
  
  
• Check tides: For shallow beaches like Anne’s Beach, high and low tides can make a big difference in your experience.

Islamorada’s tranquil beaches, island charm, and vibrant community lifestyle make it one of the most desirable places to live or invest in the Florida Keys. Whether you’re dreaming of a vacation home, planning to relocate permanently, or seeking an income-producing rental property, you need the right local expertise to guide you.

That’s where Pine River Realty comes in. Based in Miami and serving clients throughout South Florida and the Keys, Pine River Realty is your go-to partner for real estate with a personal touch. Their team understands the unique appeal of waterfront living and offers unmatched insight into some of the most exclusive and beautiful properties in the region.

From beachside condos to private island retreats, Pine River Realty has the local knowledge, network, and dedication to help you find your ideal piece of paradise. If Islamorada feels like your kind of escape, let the professionals at Pine River Realty help make it home.

Ready to explore real estate opportunities in Islamorada or anywhere in the Florida Keys? Contact Pine River Realty to start your journey today.