Islamorada, a village of six islands in the Florida Keys, offers a handful of resorts where your dog is as welcome as you are. The Islander Resort sits directly on a private beach, providing two swimming pools, a bar, and spacious rooms with private lanais. Rates hover around $250-$400 per night depending on season. Drop Anchor Resort & Marina, adjacent to Windley Key Fossil Reef Geological State Park, includes kayaks, paddleboards, and boat docking with rooms from $180 per night. These properties focus on outdoor living, so expect oceanfront pools, barbecue areas, and sandy access points rather than luxury spas or fine dining.
For a quieter stay, Bayside Villas by Islander Resort places you on Florida Bay in townhouse-style units with full kitchens and laundry facilities. Chesapeake Beach Resort offers an ocean-view pool, private beach area, and is a three-minute walk from the History of Diving Museum. Budget around $150-$300 per night at these properties. Upper Matecumbe Key is the central hub, closest to restaurants and shops, while Windley Key appeals to those wanting proximity to Theater of the Sea. Book directly with resorts to confirm pet policies, size limits, and any additional fees-most charge a one-time pet fee between $50 and $100.