Places to Stay

Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.

Little Basin Villas offers 3-bedroom, 3.5-bathroom waterfront townhomes with private balconies, a heated pool, and boat dockage in Islamorada’s Art District.

Islamorada Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.

Bud n' Mary's has been sending boats out of Islamorada since 1944, and on any given morning there are more than 40 captains and guides working these docks at mile marker 79.8. Book a charter, eat breakfast at the grill before you shove off, and sleep on a houseboat tied up right there when you get back.

Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.

White Gate Court is a charming, pet-friendly boutique resort nestled on three lush acres in Islamorada, offering seven unique cottages with old Keys-style charm.

Creekside Inn Islamorada offers cozy, comfortable accommodations with water views, complimentary Wi-Fi, and easy access to water sports. Ideal for travelers seeking a relaxed, nature-filled getaway in the Florida Keys.

Pines & Palms Resort — a boutique, ocean-front retreat in Islamorada offering a peaceful Keys-style village with cottages and suites.

Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.

Mar‑Key Islamorada is an exclusive oceanfront private estate in the Florida Keys blending historic Old Florida charm with modern luxury.

Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways

Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!

Key Lantern Motel & Blue Fin Inn offers clean, budget-friendly rooms in Islamorada, ideal for Keys adventurers.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.