By Jonathon Schaff, Travel Correspondent

Serene Waterways Surrounded by Spacious Condo Units

From a distance, it looks like the private garden of island royalty: palm trees, pink flowers, and jungle-like vegetation surround a lagoon in the middle of which sits a gazebo accessible only by wooden footbridges splayed out across the water. This is the eye-grabbing centerpiece of Park Shore Resort's canals. As the sun sets over Florida's western coast, couples stroll across the bridges and watch as pink and orange work their way into everything, spreading across the sky and reflecting off the water as ducks paddle past, indifferent to what for them is an everyday occurrence.

The sunset comes into full, showy view from the private balcony of each condo-style room, too—chairs carved with ornate pineapples on their backs provide a front-row seat. Inside, classic stucco walls surround a cozy living room and a fully stocked kitchen outfitted with speckled countertops. Natural light pours in from a wall of windows, each one capped by floral-print shades. Overnighters eventually retire to a king-size bed or a king and two twins.

The condo buildings form a perimeter around the center of the property, like the protective walls of a castle. On the center lagoon, a diverse group of animals seems to have brokered an unlikely living arrangement: as ducks swim on the pond, a cat prowls the area, and a four-foot-long iguana snacks on yellow flowers blooming beneath the waterfalls. The island also houses the outdoor pool, whirlpool, and Island Pub Restaurant. On Fridays at the restaurant, older couples in oxfords and sundresses leave melting cocktails at their tables and take to the dance floor to twist and whirl as singer Trevor Earl puts his spin on classic hits such as "Purple Rain" and "Sweet Caroline." The restaurant serves up fresh fish and specialty cakes blending crabmeat, mussels, and shrimp.

Naples, Florida: Upscale Retreat on Pristine West Coast

Bleached sand and 75-degree water clear as glass—everything seems so impeccably clean in Naples. Retirees and snowbirds saunter along the city's main boardwalk, catching up with old friends to recap their respective summers. Anglers casually cast their lines into the crystalline waters off of Naples Pier. “The main one you wanna catch is a pompano,” claims Jim from western Massachusetts, his rod resting against the wooden pier. With a sea this clear, it seems almost unfair to the fish. But by midmorning, nobody has reeled in so much as a frozen pizza—not that anybody seems to mind. East of the pier stands sunny Old Naples, where luxury cars are parked near art galleries, upscale restaurants, and bars with outdoor patios. Palm trees wreathed in holiday lights sprout from the sidewalks and shimmy in the warm breeze.

It's worth the scenic 30- to 40-minute drive south of the hotel to take in Marco Island and the Isle of Capri, home to several superb spots for seaside dining. A thatched roof crowns the screened-in patio of Capri Fish House; inside, the eclectic décor includes life preservers, sharks, sea turtles, and dozens of $1 bills inscribed with messages from past patrons. Visitors can dine here while peering out at kayaks and schooners on the sea, or park in a chair on the adjacent private beach and bury their feet in the sand. The rustic, weather-beaten feel of the eatery lends a sense of authenticity, as does the fresh mahi mahi, which comes simmered in Cajun spices and plated atop rice pilaf.