Orlando, Florida boasts endless fun in the sun and numerous world-class theme and amusement parks. However, when you want to escape the crowds and explore areas beyond central Florida, you can go hiking through the parks of Amelia Island, or paddle a kayak through the waters in St. Augustine. Most of these unforgettable destinations are within a five hours’ drive from Orlando. So book a cozy Orlando vacation rental as your home base, and prepare for an adventure of a lifetime.

a covered beach pier

1. Amelia Island

After traveling three hours from Orlando, arrive on Amelia Island, a city known for its stunning views, sandy beaches, and sparkling sunsets. Immerse yourself in the history of this small town while strolling through the Amelia Island Historic District to see unique architecture and patronize locally-owned shops. Sink your toes in the sand and then hop on a horseback ride with Happy Trails Walking Horses, which guides you right along the coast. If you’re up for an adventurous hike, head over to Fort Clinch Park for the day before retreating back to your vacation rental.

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2. Key Biscayne

Find yourself surrounded by history and spectacular views with a vacation rental in Key Biscayne, located three hours and 45 minutes from Orlando. Serenity is in your future when you sunbathe on the beaches of this barrier island, or opt for a walk through Crandon Park to spot loggerhead turtles, birds, and butterflies. Thrill seekers can fly the skies with a ride from Miami Seaplane Tours. On the ground, you can get some exercise by climbing the 109 steps to the top of the city’s lighthouse in Bill Baggs Cape Florida State Park.

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3. St. Augustine

Escape central Florida with a weekend getaway in St. Augustine, one of Florida’s oldest cities located about two hours from Orlando. Explore the waters at Crescent Beach with kayak or canoe rentals from Anastasia watersports. When you’re traveling as a couple, let your significant other sweep you off your feet with a horse-drawn carriage ride through the historic district’s cobblestone streets with Country Carriages. Get wet and wild when traveling with the kids with a boat tour from St. Augustine ECO Tours. Along the way keep an eye out for underwater creatures and exotic birds. If history is your thing, enjoy a tour of the St. Augustine Lighthouse and Maritime Museum or Castillo de San Marcos.

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4. St. George Island

St. George Island offers small-town charm with big attractions when you book a vacation rental for the weekend. After a five-hour drive from Orlando, set out to explore the ocean and dolphin watch with a boat tour from Journeys St. George Guided Boat Tours. See the city’s natural wonders on the way to St. George Island Lighthouse, which offers the perfect backdrop for a selfie or family photo. Walk along sandy beaches near your vacation rental to see the waves crashing in from the Gulf of Mexico, or explore the waters with kayak rentals from St. George Island Outfitters.

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5. St. Petersburg

Just two and a half hours in the car lands you in the beachfront community of St. Petersburg. Spend part of your weekend getaway hiking Fort De Soto Park, which has scenic trails that run along the coast. Enjoy the local art scene with a visit to the Salvador Dali Museum, or a visit to specialty shops and galleries in the Grand Central District. When hunger strikes, check out the eclectic restaurants in the city, such as Brick and Mortar, Jimmy Hula’s, and Urban Comfort, all located within minutes from numerous vacation rentals.

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6. Captiva

Settle into a cozy vacation rental in the quaint town of Captiva, which is located of the Gulf of Mexico’s mainland. This peaceful Florida city gives you and the family to enjoy some peace and quiet while fishing in the Gulf or biking around with rentals from Billy’s Rentals. Venture out into the waters for a day of sailing or kayaking, and then satisfy your hunger with a stop in at the Bubble Room, an eccentric, multi-themed restaurant on the island. If you want to take your vacation to a higher level of fun, soar through the air with a parasailing adventure with Captiva Watersports. The town is about four hours from Orlando.

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7. Islamorada

Fishing enthusiasts flock to Islamorada to take advantage of the rich waters off the five islands located in the city, which lies a little less than five hours south of Orlando. Reel in some fresh fish for dinner back at your vacation rental, or make a day of fishing with a guided excursion hosted by Sea Horse Private Charters. Islamorada offers plenty of family-friendly attractions, including a day of swimming with the dolphins at Theater of the Sea, a historical lesson at the History of Diving Museum, or a leisurely walk along the trails of Founders Park. Indulge the curious minds in your crew with a tour of the Windley Key Fossil Reef Geological State Park to see geological formations.

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