Places to Stay

Key Largo Inn offers budget-friendly, Caribbean-style accommodations with a pool, full bar, and dive shop, centrally located in Key Largo.

New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.

Set on a private 60-acre oceanfront sanctuary, this resort offers spacious one- and two-bedroom suites, a private sandy beach, Jr. Olympic pool, deep-water marina, oceanfront gazebo, and tennis/pickleball courts.

Casa Marina Key West is a historic oceanfront resort featuring elegant accommodations, beachfront amenities, and classic island charm.

Ibis Bay Resort offers a fun, colorful Key West escape with a private beach, pool, and onsite restaurant. Perfect for families, couples, and adventure seekers.

The Cabana Clubis a premier private swim and beach club offering a range of amenities including a heated/cooled pool, private sandy beach, spa/whirlpool, showering facilities, full bar, and a beach shop.

Oceans Edge Key West Resort & Marina is a luxury waterfront resort on Stock Island, featuring six heated saltwater pools, a 165-slip marina, an on-site restaurant, and complimentary shuttle service to Old Town Key West.

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

Drift Hotel is a boutique waterfront retreat in Key Largo offering modern, eco-chic rooms with bay views, complimentary kayaks, paddleboards, and bicycles, plus a private dock and fire pit. Ideal for couples and small groups seeking a tranquil, adventure-filled escape.

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.

Spacious 4-bedroom, 3-bathroom vacation homes in Marathon, FL, featuring private pools, boat slips, and access to a private beach.

Siesta Motel is a clean, family-run property in Marathon offering affordable rooms and efficiencies with kitchenettes, a pool with bar, and a relaxed tropical garden setting.

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.

The Palms Hotel – A charming historic guesthouse in Key West’s Old Town offering affordable boutique accommodations steps from Duval Street.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.