Florida Keys

iStock International

Chesapeake Beach Resort

Address: 83409 Overseas Hwy, at MM 83.5


City: Islamorada

Phone: 305-664-4662

Website: www.chesapeake-resort.com

Expert Review

This 65-room, 6.5-acre resort renovated in February 2009 blends Florida Keys charm with a beachfront resort feel, successfully walking the fine line to come off as cozy versus cramped. There's plenty of tropical décor on the property like seashell-lined walls, tiki huts, and fountains. There's also a tennis court, outdoor fitness center, two pools, laundry services, a marina, and plenty of room options, from romantic beachfront balconies to family-friendly two-bedrooms. Although you won't find any restaurants on the premises, the owners rolled out a room service program in summer 2009 with neighboring Wahoos Bar and Grill.

Tags: moderate | editor pick | beachfront

Compare Rates to Florida Keys


“Business hotels boast particularly good deals around the holidays, when they’re completely devoid of their normal clientele.”

Laura Motta Director, Deals Publishing

Sign up for the Top 25 Newsletter
to get exclusive weekly deals