Can’t-Miss Islamorada Boutiques and Shopping: A Local Guide to Florida Keys Style

Can’t-Miss Islamorada Boutiques and Shopping: A Local Guide to Florida Keys Style

Discover the best shopping in Islamorada! From coastal fashion to handcrafted art, explore the top boutiques and shops that capture the charm of the Florida Keys.

Where Island Style Meets Artisan Finds - Islamorada isn’t just a paradise for boaters and anglers—it’s also home to a vibrant shopping scene filled with coastal-chic boutiques, locally made goods, and stylish finds you won’t discover anywhere else. 

In this guide, you’ll find the can’t-miss boutiques in Islamorada, including hidden gems that locals love and visitors can’t stop raving about. Each shop reflects the personality of the islands, with offerings that range from boho clothing to nautical décor to eco-conscious skincare.

As a local real estate expert and lifelong Keys resident, I not only help people find homes in Islamorada—I help them connect with the lifestyle. That includes knowing exactly where to shop, what to buy, and how to support local businesses that make our village so special and our community so tight.

🌴 Why Shopping in Islamorada Is Different

Unlike big-box stores or crowded malls, shopping in Islamorada is intimate, personal, and deeply connected to the island’s community and culture. Many shops are owned by locals and artisans who live right here in the Keys. They curate collections that reflect the coastal lifestyle, environmental awareness, and tropical beauty of the region.

Plus, many boutiques are located near top attractions, making it easy to stroll from a gallery to a gift shop to a sunset cocktail—all in the same afternoon.

🛍️ The Best Boutiques in Islamorada (Selected with Local Love)

1. Ocean Gardens – MM 82

Category: Vintage décor, nautical antiques, coral, shells
📍 82100 Overseas Hwy, Islamorada

This Islamorada icon is equal parts museum and boutique. Ocean Gardens is packed with one-of-a-kind nautical antiques, vintage glass buoys, coral displays, shells, and maritime relics that bring the Florida Keys into your home. If you’re shopping for a statement piece or rare collectible, this is the place to make your home truly feel like Islamorad.

💡 Local tip: Ask about their antique maps and island charts—they make amazing gifts or vacation keepsakes.

2. The Islander Shoppe – MM 82.1

Category: Resort wear, beach bags, accessories
📍 Islander Resort, 82100 Overseas Hwy

Located inside the Islander Resort, this upscale boutique features resort-chic clothing, luxury swimwear, and stylish accessories that perfectly reflect the Islamorada lifestyle. It’s a great stop if you’re looking to elevate your vacation wardrobe or need a last-minute gift that doesn’t feel rushed.

3. Miss Monroe Boutique – MM 81.6

Category: Women's fashion, accessories, coastal gifts
📍 81888 Overseas Hwy, Islamorada

Trendy, feminine, and fun—Miss Monroe is your go-to for breezy Florida Keys fashion with a touch of glam. Think flowy dresses, beachy hats, and handmade jewelry. Their collection is constantly updated with new arrivals, making it a favorite among both locals and repeat visitors.

💡 Local tip: Check out the burrito shop in the back for the most amazing lunch!

4. Bella Sol Boutique – MM 82

Category: Bohemian fashion, home decor, jewelry
📍 82245 Overseas Hwy, Islamorada

Bella Sol brings Boho Keys vibes to life with handpicked apparel, artisan-crafted jewelry, and home goods. The boutique focuses on independent designers and sustainable brands, perfect for conscious shoppers who want to look good and do good.

5. The Shops at Morada Way – MM 81.5

Category: Art galleries, handmade goods, unique gifts
📍 Morada Way Arts & Cultural District, Islamorada

A must-stop for art lovers and boutique shoppers, this walkable stretch of Old Highway is home to multiple locally owned shops, including Pasta Pantaleo’s gallery, Redbone Gallery, Olga’s Boutique, and rotating artisan pop-ups. It’s a place where you can shop, meet the artists, and enjoy the village vibe that makes Islamorada so unique.

🎨 Plan your visit around the Third Thursday Art Walk for live music, pop-up markets, and new exhibit openings, plus get to meet many of the artists!

6. Sway Boutique – MM 81.6

Category: Women’s fashion, jewelry, coastal gifts
📍 Located in the Village Square at Trading Post

A stylish, well-curated boutique that blends coastal charm with contemporary style. Sway offers an elevated shopping experience with flattering wardrobe staples, handcrafted jewelry, and chic accessories. It's a favorite among locals and brides looking for island wear or special pieces.

7. Otherside Boardsports – MM 82.7

Category: Watersports gear, apparel, boards
📍 82758 Overseas Hwy, Islamorada

For the active lifestyle crowd, Otherside Boardsports is the go-to shop. Whether you're into kiteboarding, paddleboarding, or surfing, this shop has the gear, the brands, and the know-how. They also carry sporty, eco-conscious apparel and sun protection gear perfect for the Keys.

🚤 Ask about paddleboard rentals, kite surfing, and guided eco-tours on the bayside!

8. Islamorada Mercantile – MM 81.5

Category: Coastal home decor, accessories, gifts
📍 81219 Overseas Hwy, Islamorada

A fresh addition to Islamorada’s boutique scene, Islamorada Mercantile features elevated home decor, glassware, and locally inspired gifts in a beautifully designed retail space. Whether you're decorating a Keys vacation home or looking for a unique hostess gift, this shop has thoughtful pieces with a signature Islamorada flair.

9. Wild Lily Boutique – MM 81.6

Category: Women’s fashion, island-chic style
📍 Located in the Village Square at Trading Post

Wild Lily offers a curated mix of on-trend fashion with tropical flair, perfect for vacation wardrobes and everyday island living. Their inventory includes breezy dresses, statement accessories, and stylish shoes—making it easy to step into Keys confidence.

🧭 Map Your Shopping Day by Mile Marker

To help you plan your shopping itinerary, here’s a quick glance at where these boutiques are located:

• MM 82.7: Otherside Boardsports
• MM 82–81.5: Core boutique district (Ocean Gardens, Bella Sol, Islander Shoppe, Miss Monroe, Wild Lily, Sway, Shops at Morada Way, Islamorada Mercantile)
• MM 81.2: Green Turtle Inn gift shop (bonus stop)

✨ What Makes Islamorada Shopping Unique?

• 🛥️ Waterfront charm: Many shops are near marinas, beach bars, and sunset docks.
• 🖼️ Artisanal emphasis: Nearly every boutique supports local makers or independent labels.
• 🌱 Sustainable shopping: Many stores prioritize eco-conscious fashion and handmade goods.
• 🐚 Inspired by the sea: Shells, driftwood, coral motifs, and nautical touches are everywhere.

🔗 Related Islamorada Lifestyle Guides

• 40 Things to Do in the Florida Keys
• The True Cost of Living in the Florida Keys