Places to Stay

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.

Charming Key West oasis with private baths, heated pool, and prime location.

The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.

Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!

Bud n' Mary's has been sending boats out of Islamorada since 1944, and on any given morning there are more than 40 captains and guides working these docks at mile marker 79.8. Book a charter, eat breakfast at the grill before you shove off, and sleep on a houseboat tied up right there when you get back.

Old Town Suites is a boutique hotel in Key West featuring self-catering apartments with full kitchens, a coffee shop, and a prime location just steps from Duval Street and the Ernest Hemingway Home and Museum.

Colocada Vacation Rentals specializes in upscale Key West accommodations, offering nightly, weekly, and monthly rentals with VIP-level guest services rooted in generations of local expertise.

The Hilton 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.

Charming adult-only Key West retreat with pool, jacuzzi, and vibrant vibes.

Bayfront Suites in Key West offers luxury waterfront condos with modern amenities, a rooftop veranda, and a private marina. Perfect for both relaxation and special events.

Key West Historic Inns — a curated collection of five distinctive, historic properties in Old Town Key West offering boutique stays steeped in island charm.

The Saint Hotel Key West, Autograph Collection, is an adults-only boutique hotel located at 417 Eaton Street in Old Town Key West.

Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.

Sea View Estate is a secluded, oceanfront retreat on Sugarloaf Key featuring two vacation homes, a private dock, pool, tiki bar, and stunning Atlantic views just 15 minutes from Key West.

Stay in unique dual stateroom houseboats with full kitchens, A/C, and waterfront views!