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.

Keys Season Deals

Islamorada

La Siesta Resort & Marina

La Siesta Resort & Villas offers beachfront cottages, suites, and villas with pools, complimentary watersports, and access to three sister resorts in Islamorada.

Key West

Rent Key West Vacations

Key West condos and vacation rentals with full kitchens and linens—learn more.

Marathon

Key By The Sea

Pet-friendly RV/mobile-home community with canal dock access, clubhouse, bathhouse, and oceanfront pavilion.

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

Lunara Bay

Lunara Bay offers 26 luxury oceanfront estates with 6–8 bedrooms, private pools, gourmet kitchens, and concierge services in Key West.

Marathon

Keys Cove Resort | Marathon Rental Homes

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

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.

Marathon

Rentals in Paradise Inc

Discover a curated selection of vacation homes in Marathon, FL, featuring private pools, docks, and waterfront views. Ideal for families and groups seeking a relaxing Keys getaway.

Marathon

Conch Key Cottages

Conch Key Cottages offers charming waterfront accommodations on Conch Key in the Florida Keys. Guests can enjoy private cottages with boat slips, ideal for fishing and exploring nearby attractions.

Key West

Casa Del Sol, a Key West Vacation

Luxury 2-story townhome in Key West's premier Truman Annex, near Duval St.

Key West

Fitch Lodge

Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.

Islamorada

Caloosa Cove Resort

Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.

Islamorada

Casa Morada

Casa Morada is a boutique resort in Islamorada offering 16 suites with private balconies or patios, complimentary kayaks and paddleboards, and access to yoga sessions.