Places to Stay

The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.

Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.

Hyatt Centric Key West – Waterfront resort with spa, pool, and dining.

Snappers Oceanfront Restaurant & Bar in Key Largo serves vibrant waterfront dining with a casual Tiki Bar, live music, dockside seating, boat dockage, and a “Keysy” island vibe.

Coconut Mallory Marina + Resort is a laid-back, family-friendly retreat in Key West, offering studio, one-bedroom, and two-bedroom condos with full kitchens.

Adult-only Key West inn with lush gardens, pool, spa, and cozy rooms.

Tea Table Key is a spectacular, car-accessible private island estate in Islamorada, spanning over 15 acres and offering complete exclusivity just off the Overseas Highway.

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

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

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering upscale accommodations, a 9-hole golf course, spa services, and a private beach with water sports activities. Ideal for couples and families seeking a tranquil Keys getaway.

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Stay at the iconic Southernmost House, an oceanfront boutique hotel blending historic charm with unforgettable Atlantic views.

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

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.