Places to Stay

Luxury Florida Keys vacation rentals with ocean views, private pools, and 24/7 support.

The Reach Key West, Curio Collection by Hilton, is a luxurious beachfront resort situated on the island's only private natural sand beach.

Florida Keys Vacations offers family-friendly vacation rental homes and condos in Marathon and Key Colony Beach, FL—with beachfront and canal-front properties that deliver easy access to boating, snorkeling, and island living.

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.

Hampton Inn Key Largo is a tropical hotel located on Florida Bay, offering free hot breakfast, an outdoor pool, fitness center, and complimentary WiFi. Guests can enjoy a private beach, boat dock, and easy access to nearby attractions like John Pennekamp Coral Reef State Park.

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.

Courtyard by Marriott Key Largo — comfortable Key Largo hotel with full-service marina, pool, fitness center and easy access to Florida Keys adventures.

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.

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.

Silver Palms Inn is a chic, eco-certified boutique hotel in Old Town Key West, featuring lush tropical décor, an outdoor saltwater pool, complimentary breakfast, and bicycle rentals just steps from Duval Street.

Sunset Inn is a renovated boutique hotel in Islamorada offering modern rooms with island-inspired décor, a refreshing outdoor pool, and a central location near local attractions.

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.

Canal-front Key Colony Beach: sleeps 4, private dock, Cabana Club access.

Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.