Accommodations in Key West

Hotels, resorts, guesthouses, and vacation rentals.

Top Accommodations Listings

  • Southernmost Beach Resort — Oceanfront resort at the end of Duval Street where Old Town meets the Atlantic. Multiple pools, private beach access, and steps from the Southernmost Point buoy. Social atmosphere with resort energy, perfect for travelers who want beach and nightlife in one location. (4.3/5, 431 reviews) | 1319 Duval Street, Key West, FL 33040
  • The Marquesa Hotel — Luxury boutique hotel in beautifully restored historic conch houses, one block from Duval Street. Three swimming pools surrounded by lush tropical gardens, and home to the award-winning Café Marquesa restaurant. Adults only (14+), smoke-free, with free off-street parking. (4.8/5, 134 reviews) | 600 Fleming Street, Key West, FL 33040
  • The Saint Hotel Key West — Adults-only boutique hotel in the Marriott Autograph Collection. 36 stylishly designed rooms just off Duval Street with rooftop lounge Halo, outdoor pool, and Tempt restaurant. Contemporary design with boutique energy and the backing of a trusted brand. (4.5/5, 165 reviews) | 417 Eaton Street, Key West, FL 33040
  • The Gardens Hotel — Adults-only luxury boutique hotel set on over one acre of tropical gardens. 17 elegant suites and cottages with Bahamian plantation-style design, two pools, d'Vine Wine Gallery, and complimentary breakfast. One block from Duval Street. Originally the largest private estate in Key West, established in 1930. (4.8/5, 110 reviews) | 526 Angela Street, Key West, FL 33040
  • Casa Marina Key West — Historic 1920 landmark resort with 311 renovated rooms and one of the largest private beaches in Key West. Curio Collection by Hilton with multiple pools, spa services, and oceanfront dining at Dorada. Classic grand resort atmosphere on the Atlantic, recently renovated. (4.3/5, 123 reviews) | 1500 Reynolds Street, Key West, FL 33040
  • Simonton Court Historic Inn & Cottages — Adults-only tropical oasis on two acres in Old Town, two blocks from Duval Street. Victorian and Conch architecture with four secluded pools, lush gardens, cottage-style layout, complimentary breakfast, and bicycle rentals. A hidden gem for romantic, laid-back stays off the busy streets. (4.7/5, 78 reviews) | 320 Simonton Street, Key West, FL 33040
  • Vacation Homes of Key West — Locally owned since 1997 by three generations of native Key Westers. Fully furnished homes with private pools, beach access, and concierge services. Book direct for 10%+ savings over third-party sites. Weekly and monthly rentals available — popular with snowbirds and remote workers. (4.7/5, 77 reviews) | 507 Whitehead Street, Key West, FL 33040
  • The Reach Key West — Sister property to Casa Marina, located on the only private natural sand beach in Key West. Curio Collection by Hilton with 150 nautically-inspired rooms, oceanfront dining at Four Marlins, and walking distance to Duval Street and Old Town. Perfect for beach lovers who want direct sand access. (4.3/5, 83 reviews) | 1435 Simonton Street, Key West, FL 33040
  • Opal Key Resort & Marina — Waterfront resort in Old Town with 178 rooms, a 37-slip marina, pool, and multiple dining options. Steps from Mallory Square and one block from Duval Street, adjacent to the Key West Aquarium. Prime harbor location with sunset proximity and walkable to everything. (4.2/5, 89 reviews) | 245 Front Street, Key West, FL 33040
  • Last Key Realty — Over 50 vacation rentals including homes, condos, and villas throughout Key West. Properties in Historic Old Town, Truman Annex, and on Duval Street with 24/7 personalized concierge services. Daily, weekly, and monthly stays with pet-friendly options and private pools. (4.6/5, 44 reviews) | 825 Duval Street, Key West, FL 33040
  • Best of Key West Rentals — Luxury homes, condos, cottages, and historic estates throughout Key West. Nightly rentals with a 4-night minimum, monthly stays, pet-friendly accommodations, and properties with private pools. Professional staff with 24/7 property management services. (4.5/5, 38 reviews) | 1205 Truman Avenue, Key West, FL 33040
  • Preferred Properties Key West — Locally owned boutique agency with over 20 years of experience in Key West vacation rentals. Specializing in homes with private pools, outdoor spaces, and easy Duval Street access. Located in the heart of Old Town with personalized service and local expertise. (4.7/5, 32 reviews) | 520 Southard Street, Key West, FL 33040
  • Your Keys Vacation Rentals — Curated collection of luxury vacation homes in Key West's Old Town. Beautifully renovated conch-style residences with private pools, full kitchens, and modern amenities — all within walking distance of Duval Street. Specializing in monthly rentals for extended stays. (4.8/5, 24 reviews) | Key West, FL 33040
  • Ocean Key Resort & Spa Weddings — An oceanfront Key West wedding venue at the foot of Duval Street, with ceremonies and receptions on the iconic Sunset Pier and Ocean Terrace, dedicated event support, and catering from Hot Tin Roof. | 0 Duval Street, Key West, FL 33040
  • The Perry Hotel & Marina Weddings — A marina-front Stock Island venue with more than 20,000 square feet of flexible event space, tropical outdoor settings, reception options, and a distinctive working-waterfront atmosphere. | 7001 Shrimp Road, Key West, FL 33040