Places to Stay

Conch Key Landing — waterfront vacation-rental cottages with private dockage and stunning Florida Bay views on Conch Key.

Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.

Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.

Southwinds Motel is a budget-friendly, adults-only hotel in Old Town Key West, offering two outdoor pools, complimentary continental breakfast, and convenient access to Duval Street and the Atlantic Ocean.

Marrero’s Guest Mansion is an adults-only boutique B&B in Old Town Key West, offering unique rooms in a restored Victorian mansion with a saltwater pool.

Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.

Locally owned vacation rental company offering a variety of homes and condos in Marathon, FL. Features include private pools, pet-friendly options, and concierge services.

Vacation Homes of Key West is a locally owned boutique vacation rental company offering a curated collection of authentic island-style homes.

Conch Key Villas offers charming waterfront accommodations on Conch Key, featuring fully equipped studios with private boat slips, ideal for fishing enthusiasts and couples seeking a tranquil retreat.

Little Torch Cottages offers 2-bedroom townhomes with full kitchens, private balconies, and access to two tropical pools in the Florida Keys.

The Ocean View Inn & Sports Pub in Islamorada offers comfortable accommodations with a tropical flair, an outdoor pool, and a lively pub serving classic American fare and late-night bites.

Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.

Curated Florida Keys vacation homes and island escapes in Key West, Key Largo, Marathon, and beyond — combining comfort, local charm, and personalized service for every traveler.

Charming Old Town Key West villas and B&B suites with pool.

Colors on White offers vibrant, apartment-style accommodations in Old Town Key West. Each unit features a private entrance, kitchenette, and access to a pool with a cascading waterfall.