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
Marathon
Captain Pip's Marina & Hideaway
Captain Pip’s Marina & Hideaway offers waterfront accommodations in Marathon, FL, featuring cozy rooms and 1- and 2-bedroom apartments with kitchenettes.
Islamorada
Mar-Key Islamorada
Mar‑Key Islamorada is an exclusive oceanfront private estate in the Florida Keys blending historic Old Florida charm with modern luxury.
Meetings Max
20
Marathon
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Key Largo
Azul Del Mar
Secluded Key Largo boutique resort with romantic suites, waterfront fun, and stunning sunsets.
Weddings Max
60
Key Largo
Star Properties Destinations
Star Properties Destinations is a vacation rental and property management company in the Florida Keys, offering a variety of accommodations across Key Largo, Islamorada, Marathon, Tavernier, and the Lower Keys.
The Lower Keys
Captains Quarters
Captain’s Quarters #415 — stylish 2-bedroom waterfront rental in the gated Venture Out community on Cudjoe Key, Florida Keys.
Key Largo
Bungalows Key Largo
All-inclusive adults-only luxury resort in Key Largo with oceanfront bungalows.
Meetings Max
40
Total Space
2800 sq ft
Largest Room
2800 sq ft
Islamorada
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Key West
Havana Cabana Key West
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 West
Margaritaville Beach House Key West
Margaritaville Beach House Key West offers laid-back, island-inspired accommodations steps from Smathers Beach, with a lagoon-style pool and on-site bar & grill.
Weddings Max
100
Meetings Max
60
Total Space
4000 sq ft
Largest Room
950 sq ft
Key West
Coconut Mallory Resort & Marina
Coconut Mallory Marina + Resort is a laid-back, family-friendly retreat in Key West, offering studio, one-bedroom, and two-bedroom condos with full kitchens.
Key West
Caribbean House Hotel
Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.
Key West
Rent Key West Vacations
Key West condos and vacation rentals with full kitchens and linens—learn more.
Marathon
Dolphin Vacation Rental Homes
Dolphin Vacations offers a curated selection of vacation rentals in Key West and Marathon, FL, including historic homes and modern condos. Properties like Casa Rosa provide private pools and prime locations near Duval Street.
