Off the Beaten Path: 6 of the best vacation rentals in Florida

Miles upon miles of white sand beaches, non-stop sunshine, and endless possibilities for fun and adventure for all ages are just some of the reasons Florida is the ideal year-round vacation destination.

Whether you want to soak up the culture in North America’s oldest city, enjoy one-of-a-kind experiences off the beaten path, or eat Key Lime Pie at a favorite local haunt, you can do it all – and so much more!

No matter if you’re beach bound or city hopping, vacation rentals in Florida abound and there is an option out there for you. To make your life easier when it comes to choosing a rental home, we’ve handpicked a selection of Florida‘s best.

Jaw-dropping beach house rental in North America's oldest city

If you’re looking to vacation in stylish surroundings in an unrivaled location, Sea Spray Beach House is ideal. The 5-bedroom contemporary vacation home is located close to the charming city of St. Augustine. It accommodates up to 17 guests and is perfect for large families, reunions, and special occasions.

It’s spread across three floors with plenty of room to roam, with a stunning roof deck overlooking the ocean, oversized pool, and firepit below. The house is only a block from the beach where you can spend leisurely days surfing or swimming in the waves. Pets are welcome too.

At over 450 years old, St. Augustine is the oldest city in North America. One of the best ways to learn about its rich history is to take a narrated tour on an open-air trolley. You can hop on or off at any of the stops to explore at your leisure. Make sure you visit the Colonial Quarter and St. Augustine Lighthouse.

Aviles Street is a treasured gem with eclectic art galleries, craft boutiques, and plenty of eateries offering alfresco dining. Forgotten Tonic is a cool spot with an impressive craft cocktail menu. When kids start to flag, stop off at Peace Pie for the best ice cream sandwich you’ll ever eat.

If you love adventures on the water, book a boat ride that combines a fascinating history tour and the chance to see dolphins and sea turtles. Another fun option is a kayaking trip, where you’ll paddle along the bay front past the old fort Castillo de San Marcos and into the salt marshes. For those who feel like getting up close to Florida’s iconic alligators, head to St. Augustine Alligator Farm. The best way to see them is on the zipline.

Sea Spray Beach House, 5 Bedrooms, Private Pool, Sleeps 17

St. Augustine Beach

Lavish rental villa with 5-star amenities located minutes from Walt Disney World

This 9-bedroom luxury rental home is perfect when you want to bring grandparents, cousins, or anyone else. Located at Encore Resort at Reunion, Villa Ec005 offers the space and privacy of a private home with all the amenities of a five-star resort. Guests have access to the resort’s clubhouse and aqua park. It is minutes from Orlando’s top theme parks, with Walt Disney World only a 6-minute drive away.

The stylish interior includes a Star Wars-themed games room with a ping pong table. There’s also a pool and jacuzzi.

Although Central Florida’s theme parks are often the main attraction, there’s so much more to explore. Thrill-seeking kids will love Orlando Tree Trek, which is close by, or you can head to Wild Florida for an airboat ride and drive-thru safari.

For a more leisurely adventure, Lake Eola Park offers paddle boat rides. At Winter Garden, you can to rent bikes (with trailers for little ones) and cycle through the fields and forest canopies of the West Orange Trail. Stop for lunch at Plant Street Market, a local artisan market with plenty of outdoor space for kids to play.

If you’re looking for a completely different experience, the Showcase of Citrus (a working citrus and cattle ranch) is not to be missed. As well as monster truck rides, you can pick your own fruit.

Villa Ec005 -Your Villa With Private Pool & Spa- 9 Bedroom Villa

9.0 Excellent (8 reviews)

Romantic rental escape for two in the heart of Key West's Old Town

Enjoy a romantic escape for two at this luxury penthouse apartment in Key West, the southernmost island in the Florida Keys. Penthouse R19 benefits from a shared pool for those days when you feel like doing as little as possible. The apartment has a private hot tub, deck, and balcony, so you have a choice of where to enjoy an evening cocktail. It is just a mile from Fort Zachary Taylor Historic State Park to the west and two miles from Smathers Beach to the east.

Key West is a sub-tropical paradise known for its mix of history, vibrant nightlife, and laid back vibe. The apartment is conveniently located in Duval Square in the heart of the old town.

The Ernest Hemingway Home and Museum and Nancy Forrester’s Secret Garden, a sanctuary for rescued parrots, are both worth a visit. To get a real feel for this little island, there are a variety of tours you can take, whether you’re into food, ghosts, or culture. If you love the water, you can go snorkeling in the Dry Tortugas National Park, dolphin watching, or deep-sea fishing.

The sun sets on the west side of the island, where the Atlantic Ocean meets the Gulf of Mexico. One of the best spots to watch it sink beneath the horizon is Mallory Square, where locals and tourists gather for the nightly sun celebration – a festival complete with live music and street performers.

Of course, you can’t leave the island without trying the legendary Key Lime Pie and Sarabeth’s has some of the best.

Penthouse W/ Private Hot Tub & Shared Pool - Close To Beaches, Dogs Ok.

Key West
8.0 Very good (76 reviews)

The ultimate beachfront rental escape on an enchanting island

For milestone birthdays, weddings, or any other special occasion, you’ll want to snap up this jaw-dropping 11-bedroom vacation home on Captiva. Sea Oats Luxury Estate was named #1 in Coast Living Magazine’s “10 Best Beach House Rentals in Florida”. The four acre island paradise is steps from the beach and comes with all the amenities you could wish for, including an oversized pool, tennis and basketball courts, a golf cart, and a dock. It also comes with a personal concierge service to arrange private chefs, yoga classes, and in-home massages.

The island of Captiva has a relaxed, old Florida atmosphere with unspoiled beaches and a wealth of outdoor activities. There is an array of private experiences to suit all ages and interests for guests. One day, you could be on a deep-sea fishing trip or a sunset cruise right from your dock. The next, you could set off on a kayaking or paddle boarding adventure through Pine Island Sound and Calusa Blueway Paddle Trail, home to manatees and dolphins.

As the sun goes down, islanders and tourists gather for the Mucky Ducky Duck, a nightly festival where you can enjoy fresh seafood and live entertainment. When you feel like dining out, the Bubble Room Restaurant and Emporium is a magical experience for the whole family that you won’t want to miss.

Sea Oats Captiva Island

Top rated
Captiva Island
9.5 Excellent (26 reviews)

New Miami-style rental retreat close to Olde Naples

If you’re looking for a stylish family retreat that’s close to shops, restaurants, and the beach, the Close to Olde Naples Beaches Exclusive Designer Home checks all the boxes. This newly built, 4-bedroom vacation home is located in Royal Harbor on the famous Naples Bay, close to the old town. The property boasts a heated pool, hot tub and gourmet outdoor kitchen.

Located on the Gulf of Mexico in Southwest Florida, Naples is famous for its high-end boutiques, culture, and top-notch Italian food. It is also an affordable family destination that appeals to nature lovers with miles of beaches where you can take the kids.

There’s so much to do on the water too, from private fishing charters to a catamaran ride to Keewaydin Island – the perfect spot for shelling. Some of the restaurants, such as Bay House, will even cook and serve up your catch.

For one-of-a-kind experiences the whole family will enjoy, book a guided kayak tour into the mangroves at Rookery Bay or an airboat tour through the everglades. The Shy Wolf Sanctuary is also worth a visit. For those who prefer retail therapy, hit the boutiques on 5th Avenue and 3rd Street in downtown Naples.

Close To Olde Naples Beaches Exclusive Designer Home

9.0 Excellent (8 reviews)

Luxurious waterfront townhouse rental near the beach

This beautiful 4-story waterfront townhouse is located at the south end of Clearwater. It’s just a short stroll from the pristine white sand beach that stretches three miles along the coastline and is classed one of the best in the world.

The 3-bed property is ideal for families and spacious enough to bring the grandparents, if you wish. It has a private rooftop terrace with a hot tub overlooking the waterways and the ocean, as well as its own elevator and a shared pool. It’s only four blocks from Pier 60, where there’s live music every evening and locally owned craft stores.

Located just west of Tampa on the Gulf of Mexico, Clearwater has plenty on offer for families and you can do as much or as little as you wish. Kids will love the Clearwater Marine Aquarium where they can visit Winter, the famous dolphin with a prosthetic tail who inspired the movie Dolphin Tale.

For an unforgettable experience, take the ferry to Caldesi Island where you can spend the day on its secluded beaches, explore the sand dunes, or rent kayaks to go for a paddle through the bayside mangrove forest.

A visit to St. Petersburg is a must for art lovers. It’s is only a short drive away and is home to the impressive Dali Museum. It’s also worth doing a tour of the city’s mesmerizing street art.

Beautiful 4 Story Waterfront Townhouse!

9.5 Excellent (23 reviews)