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Florida Twin-Centre Trips: The Best Villa Holiday Pairings

  • By Tammy van der Westhuizen
  • Published 20 June 2023
  • Revised 31 August 2023
Florida Twin-Centre Trips: The Best Villa Holiday Pairings
  • By Tammy van der Westhuizen
  • Published 20 June 2023
  • Revised 31 August 2023
Florida Twin-Centre Trips: The Best Villa Holiday Pairings
  • By Tammy van der Westhuizen
  • Published 20 June 2023
  • Revised 31 August 2023
King-sized bedrooms with ensuite bathrooms, pools with spillover spas, open plan living with fully equipped kitchens - a dream villa holiday are all about the perfect pairings. 

And why stop there? Pair two villa holidays together and you can balance bustling cities with beach-side bliss or wallet-friendly accommodation with a luxurious resort. 

At Ocean Florida, we let you personalise almost every aspect of your holiday.

From our collection of over 2,000 Florida villas, you can choose your exact home, amenities, and precious family memories. To help inspire your choices, here are a few twin-centre Florida holidays that we think could be right up your street...

Orlando and Anna Maria Island

Best for all ages

For the perfect balance of thrills and chills, head to the Theme Park Capital of the World, Orlando, before stepping back in time to a low-rise, restorative retreat at Anna Maria Island. Plus, with a distance of 126 miles between the destinations, it could also be the perfect road trip from Central Florida to the pristine Gulf Coast.

Anna Maria Island is known for its laid-back charm, in part due to its laws which limit the height of structures to maintain the island's natural beauty. This natural beauty includes a seven-mile stretch of powder-white sand and an uncrowded coastline will give you the sense of having the beach all to yourself.

Plus, with villas situated moments away from the beach, you’ll get to enjoy the ambience of whispering waves and aquamarine shores whenever you please. At our collection of palm-tree-lined Anna Maria Island villas, you can also take a refreshing dip in resort-worthy private pools to ensure you reach holiday bliss. 

While in Orlando, you will of course be spoilt for choice with a range of villa communities. You can stay as close as 5 miles to Walt Disney World at Emerald Island Resort, or opt to stay further out in a quiet conservation area at Watersong Resort. From resorts with championship golf courses to exciting water parks and those offering shuttle transport to Walt Disney World Resort, we can help you find the perfect villa community to suit your style of holiday.

Fort Myers and Sanibel

Best for beach babes & history buffs

The gateway to Southwest Florida, Fort Myers is a beach lover’s destination with great shopping malls and outdoor nature attractions. Enjoy the convenience of a villa home with a full kitchen and private swimming pool, and pair it with the comforts of staying in a city with fun attractions for the whole family. 

Explore the Edison and Ford Winter Estates’ historic houses and bountiful gardens. Home to America’s two great inventors, Thomas Edison and Henry Ford, learn about their creations at the museum, showcasing old artefacts and educational exhibits. Budding scientists can experiment to their heart’s content at the IMAG History & Science Center, and for outdoor activity, take the whole family on a paddle through the Calusa Blueway.

Then pack your bags and bundle in the car for 23 miles to the shelling shores of Sanibel Island. Staying in a two-bedroom condo on the Punta Rassa Peninsula, you’ll be awarded scenic views of San Carlos Bay from your private balcony and a strip of private beach out front. Drive over Sanibel Causeway to reach the seashell capital of the world, known for its secluded shores and protected nature. We can assure you that you’ll never want to leave this heaven on Earth.

Naples and Marco Island

Best for natural & a touch of luxury

A gem of Southwest Florida, Naples oozes luxury and dazzling charm with its upscale ambience. The southernmost city on Florida’s Gulf Coast boasts plentiful golfing greens, pristine beaches, and the grand Naples Waterfront. Swap your swimsuit for your hiking boots and explore inland into the Everglades National Park and Big Cypress National Preserve.

And for an even more upscale escape, head 18 miles south to Marco Island Area Villas. Here, you can stay in a stunning villa overlooking the sapphire straits, and enjoy an average of 264 days of replenishing sunshine each year. 

Marco Island is the largest of the Ten Thousand Islands, and you can explore the other enclaves of this archipelago by simply grabbing a kayak. Or, take a boat tour for your best chance to view the resident dolphins and manatees of Marco Island’s waters. And if you’re a seafood aficionado, you’ll be hard-pressed to find a better crab, oysters, and catch of the day. Best of all, you get to completely unwind in your lavish villa home, far away from bustling city centres.

Siesta Key and Charlotte Harbor Area

Best for lovers of all things outdoors

By now, you'll know that Florida is synonymous with gorgeous beaches. With this in mind, it can be hard to choose which immaculate bay to visit. But a good starting point is discovering the Sunshine State’s most award-winning shores, and Siesta Key Beach is a worthy frontrunner. Voted Tripadvisor’s Number 2 USA Beach in 2023 and the 14th best beach in the world, Siesta Key Beach boasts crystal clear waters and soft quartz sand that stays cool under the sun.

Staying at The Anchorage at Siesta Key, you’ll be within minutes of Florida’s top beach. From your two-bedroom condo, you can delight in stunning views of Siesta Key’s waterways, as well as access to the resort’s swimming pool, fitness centre, and tennis courts. Situated adjacent to Siesta Key South Village, you’ll find ample dining and shopping options.

Then head 49 miles south to Charlotte Harbor Area, staying in a villa overlooking the canals of Punta Gorda. Here, you can boat or kayak on the waterways, venture into Charlotte Harbor Preserve State Park’s mangrove wetlands, or go hiking or biking in this pristine park. Lovers of the outdoors will love this charming canalside community, leaving you feeling like you’ve truly got away from it all.

Honourable Mentions

Some prime Florida destinations are tailormade for hotel holidays, and for the best of both worlds, we offer twin-centre trips combining hotel and villa destinations, such as…

Miami and Bradenton

Best for nightlife & a slice of culture

Miami's beachfront hotels are iconic for good reason. For example, at the Newport Beachside Hotel, you can stand in the footsteps of famous guests like Jimi Hendrix, listening to the sweet symphony of ocean waves. Yet there's much more to Miami than its golden sands and party atmosphere. We recommend you also take a moment to marvel at its ice-cream-coloured Art Deco architecture and embark on a culinary tour in Litte Havanna.

Then, for a change of pace and scenery, travel 42 miles to Bradenton and stay at Shorewalk Vacation Villas. With days, you will be swept away by the city’s relaxed pace of life as you admire the Manatee River from the Riverwalk, experience a cultural immersion at Village of the Arts, and discover ancient fishermen’s tales at Cortez Historic Fishing Village. And with Sarasota’s artsy city only 12 miles away, you could even make it a multi-centre adventure.

Ready for your Floridian escape? View our Florida Villa Holidays for 2024 and 2025 for a Sunshine State of Mind in minutes.

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