Places to Stay

Claim your corner of The Florida Keys & Key West. Waterfront resorts, tucked-away inns, vacation rentals with a dock out back, campgrounds under the palms...however you like to unwind, there's a place here that gets it. Filter by destination, amenities or whatever matters most and find the spot that turns your trip from planned to perfect. Checkout is the only thing that should stress you out.

Islamorada

Keys Holiday Rentals

Keys Holiday Rentals offers vacation homes and condos in Islamorada, Florida Keys, perfect for waterfront stays, fishing trips, and family getaways.

Key West

Andrew's Inn & Garden Cottages

Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.

Key Largo

The Pelican, Key Largo Waterfront Cottages

The Pelican Key Largo Cottages is a charming waterfront retreat located directly on Florida Bay in Key Largo, offering a serene and tropical escape just an hour from Miami International Airport.

Key West

Southernmost House

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

Weddings Max

Key West

Seascape Tropical Inn

Seascape Tropical Inn is an adults-only, Conch-style bed & breakfast just steps from Duval Street, offering tropical charm, a heated pool and spa, and a complimentary breakfast with Champagne mimosas.

Marathon

Safe Harbor Marathon

Experience the ultimate Florida Keys marina with luxury amenities and stunning views.

Islamorada

Tea Table Key Island Estate & Wedding Venue

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.

The Lower Keys

Sugarloaf Key Hotel at KOA Resort

Tropical seaside stay with marina access and on-site dining.

Key West

Casa 325

Casa 325 is a charming boutique guesthouse in the heart of Key West’s Historic Old Town. Tucked just off lively Duval Street, it offers uniquely designed rooms, a pool, and easy access to shops, dining, and attractions.

Marathon

La Casa Habana Vacation Rental

La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.

Key West

Nyah B&B

NYAH Key West is an adults-only hotel offering group-friendly rooms, three pools, complimentary breakfast, and a prime location just steps from Duval Street.

Key West

Heron House

Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.