Places to Stay

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

Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!

Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.

Island Bay Resort is an adults-only boutique escape with tropical cottages, a private beach, and free kayaks & SUPs.

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

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.

Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.

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

The Islands of Islamorada is a luxurious, boutique resort nestled in the Upper Florida Keys, offering a serene and upscale escape for travelers seeking both relaxation and adventure.

Sunset Inn is a renovated boutique hotel in Islamorada offering modern rooms with island-inspired décor, a refreshing outdoor pool, and a central location near local attractions.

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

Stay in unique over-water Aqua Lodges at Treasure Harbor Resort, your private marina gateway to stunning Florida Keys adventures.

Bayside Villas by Islander Resort offers fully renovated, two-bedroom townhouse-style accommodations in Islamorada, featuring a bayview pool, water sports access, and private boat slips. Ideal for families, friends, and extended stays.