Places to Stay

Discover Winslow’s Bungalows: a vibrant, historic Key West oasis with pools, charm, and local tales.

Cuban vibes meet Key West charm—discover Havana Cabana.Havana Cabana at Key West is a Cuban-inspired hotel featuring the largest pool in Key West, a poolside bar, and a food truck serving Cuban cuisine.

Waterside Suites & Marina offers spacious, two-floor townhouse-style suites with full kitchenettes and waterfront balconies on a tranquil marina—perfect for extended stays, family getaways, or fishing enthusiasts.

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.

Gulf View Waterfront Resort offers a laid-back, Old Florida experience with spacious rooms featuring kitchenettes, an oceanfront pool, complimentary kayaks and paddleboards, and pet-friendly accommodations.

Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.

Old Wooden Bridge Resort & Marina in Big Pine Key offers charming houseboat-style accommodations, a marina, an outdoor pool, and a prime location near the No Name Key Bridge and the National Key Deer Refuge.

The Galleon Resort & Marina is a waterfront resort in Old Town Key West offering spacious studios and suites with full kitchens or kitchenettes, a private beach, pool, and on-site marina—all just steps from Duval Street.

Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.

Kona Kai Oasis offers boutique guesthouse accommodations with a pool, complimentary bikes, and lush botanical gardens in Key West’s Old Town.

Sun Outdoors Key Largo: year-round, all-ages RV resort with a marina.

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

Luxury beachfront escape with stunning views and top amenities awaits you!

Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.

Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.