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.
Filters
Islamorada
Casitas at Cheeca Lodge
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering upscale accommodations, a 9-hole golf course, spa services, and a private beach with water sports activities. Ideal for couples and families seeking a tranquil Keys getaway.
Key Largo
Florida Keys Luxury Rentals
Florida Keys Luxury Rentals offers high-end vacation homes throughout the Keys, pairing luxury accommodations with personalized concierge, private boating, fishing, gourmet meals, and diving experiences.
Key West
Fitch Lodge
Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.
Marathon
Gulf View Waterfront
Gulf View Waterfront Resort offers a laid-back, Old Florida experience with spacious rooms featuring kitchenettes, an oceanfront pool, complimentary kayaks and paddleboards, and pet-friendly accommodations.
Key West
Havana Cabana
Cuban vibes meet Key West charm—discover Havana Cabana.Havana Cabana at Key West is a Cuban-inspired hotel featuring the largest pool in Key West, a poolside bar, and a food truck serving Cuban cuisine.
Weddings Max
150
Meetings Max
60
Total Space
1820 sq ft
Largest Room
1100 sq ft
Key Largo
Dream Bay Resort
Dream Bay Resort is a private, gated resort and wedding venue in Key Largo, offering five charming cottages, a small marina, and breathtaking sunset views over Florida Bay. Ideal for romantic getaways and intimate weddings.
Key West
Andrew's Inn & Garden Cottages
Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.
Marathon
Caribbean Soul Charters
Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!
Marathon
Fairfield by Marriott Inn & Suites Marathon Florida Keys
Waterfront hotel in the Florida Keys with pools, marina, and tropical dining.
Key West
Westwinds Inn
Westwinds Inn is a charming, adults-only Victorian-style boutique hotel located in the Historic Seaport District of Old Town Key West.
Marathon
Keys Ocean Vacation Rentals
Florida Keys escapes—discover, book, plan with Keys Ocean Vacation Rentals.
Key West
Eden House Hotel
Eden House Key West is a boutique hotel in the heart of Old Town, offering a heated pool, tropical gardens, and walking distance to Duval Street. Ideal for couples seeking a charming, relaxing retreat.
Key West
Lighthouse Hotel
Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.
Weddings Max
60
Meetings Max
60
Key West
Authors Guesthouse
Stay inspired in a charming Key West guesthouse honoring literary legends.
