Chesapeake Beach Resort - Islamorada

Private oceanfront resort in Islamorada with complimentary water sports and two heated pools

Private Beach & Water Sports

The Chesapeake Beach Resort provides a private beach area with reserved loungers and pool towels for guests. Complimentary rentals include kayaks, paddleboards, and fishing poles, with bait available for purchase at the front desk. Guests can launch kayaks and paddleboards directly from the private beach.

Accommodations

The Chesapeake resort Islamorada offers spacious two-bedroom villas and premium ocean-view suites with private balconies. Each room includes a 37-inch flat-screen cable TV and a small refrigerator; some villas have a kitchenette. A personalized breakfast delivery service is available for guests ordering from the complimentary breakfast menu.

Dining & Breakfast

Each morning, the Chesapeake hotel serves a complimentary breakfast with made-to-order omelets, fresh fruit, and pastries. The on-site snack bar offers wine, champagne, and light bites, and the bar cart provides liquor options. Breakfast can be enjoyed on the outdoor terrace with ocean views, with live music on select nights.

Location & Nearby Attractions

The History of Diving Museum is a 3-minute walk from the Chesapeake Bay Islamorada, and Windley Key Fossil Reef Geological State Park is 2 miles away. Theater of the Sea is a 4-minute drive, and multiple local restaurants like Wahoo's and Papa Joe's are within walking distance. The resort is situated on the oceanfront in Islamorada, providing access to fishing charters and sunset cruises.

Additional Amenities & Services

Two heated outdoor pools with ocean views are open year-round, along with a hot tub and sun loungers. Live music performances, yoga classes, and board games are offered on-site for guest entertainment. Pet-friendly accommodations are available for a $50 nightly fee, and AAA and CAA members receive discounts and perks.

• Private Beach: Complimentary loungers, towels, and water sports rentals
• Rooms: Two-bedroom villas and ocean-view suites with balconies
• Breakfast: Made-to-order omelets and personalized room delivery
• Location: Walk to History of Diving Museum and local dining
• Activities: Kayaking, paddleboarding, fishing poles, yoga classes
• Pet-friendly: $50 nightly pet fee with dedicated accommodations