Places to Stay

Key West villas steps from Duval Street, private pool, pet-friendly.

The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.

KeysCations offers a curated selection of luxury vacation homes in Marathon, FL, featuring private pools, docks, and ocean views. Ideal for families and groups seeking a tranquil Keys getaway.

Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.

Grassy Key RV Park & Resort offers waterfront RV sites with full hookups, a heated and chilled pool, a private sandy beach, and access to Gulf and Atlantic waters, all just 45 minutes from Key West.

The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.

New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.

Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.

Kon Tiki Resort offers waterfront cottages with private boat dockage, heated pool, and a private lagoon in Islamorada, Florida Keys

Sun Outdoors Marathon: waterfront RV resort with marina and Gulf views.

Discover Jolly Roger RV Resort: spacious sites, stunning views, and island adventures!

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.

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

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.