Places to Stay

Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.

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.

The Bishop Hotel in Key West offers a boutique guesthouse experience across five historic Conch-style properties, blending Old Town charm with modern comfort.

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.

The Grand Guesthouse is an adults-only bed and breakfast in Key West, offering tropical-themed rooms with private entrances, complimentary continental breakfast, and a central location near Duval Street.

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.

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.

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.

Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.

Vacation Rentals Florida Keys — vacation homes, condos & waterfront retreats throughout the Florida Keys, where you’ll find turnkey island stays with amenities, docks and fully‑equipped kitchens.

H2O Suites is an adults-only luxury hotel in Key West, offering 22 contemporary suites with private plunge pools, Italian marble bathrooms, and rooftop pool access, just steps from Duval Street.

Luxury Florida Keys retreat for inspiring executive escapes and unforgettable vacations.

Casa Clara Condos in Key Colony Beach offers oceanfront 2-bedroom, 2-bathroom condos with private balconies, a heated pool, tennis courts, and beach access. Ideal for both short and long-term stays.

Margaritaville Beach House Key West offers laid-back, island-inspired accommodations steps from Smathers Beach, with a lagoon-style pool and on-site bar & grill.