Best 15 Getaways in Southwest Florida


A trip to Southwest Florida is not one that can be rushed. There are too many amazing places to visit, unique things to do, and experiences to fall in love with. Every city, island, and beach has its own distinct vibe, and you're sure to find a favorite (or several) that you'll want to visit again and again. As a starting point to discovering some of the region’s most stunning destinations, here are 15 of the best getaways in Southwest Florida: 


Anna Maria Island 


No matter the season, you'll love the serene beaches, fresh seafood, and laid-back atmosphere that await you along the seven miles of white sandy beaches on this barrier island. 

Anna Maria Island



Arcadia offers a little bit of cowboy culture in the heart of Florida. For years, cattle were raised here, and today it's home to the annual Fall Rodeo and Arcadia All-Florida Championship Rodeo. 


Bonita Springs


Private and secluded, Bonita Springs retains all the natural beauty and wonder that attracted the state’s very first residents. Plan a trip filled with scenic paddling, fantastic fishing, and quality time with your favorite people.




Scenic and laid-back with a focus on the arts, Bradenton is the epitome of Florida charm for many people. Stroll through any number of neighborhoods to browse art galleries, shops, cafes, and museums. 


Cape Coral


Take the kids to Cape Coral once and they'll beg to return year after year! This is the place to visit if you don't want to think about what’s next — because there’s always something! Visit Mike Greenwell's Family Fun Park or Sun Splash Family Waterpark for non-stop adventure.


Everglades City


Come explore a habitat that is unique to Southwest Florida with Everglades City as your starting point. From here you can canoe through mangrove tunnels, take a fishing or backcountry tour, or hike through Big Cypress National Preserve. 

Everglades City

Longboat Key


If luxury living is more your speed, pack your best shoes and head to Longboat Key for a taste of the finest dining, golfing, and resort living on the coast. 


Marco Island


For an unspoiled and completely luxe beach experience, visit Marco Island, right near Naples and the only developed land of the Ten Thousand Islands. 




Florida is all about the laid-back, casual lifestyle, but Naples layers luxury and sophistication on top of it. You won't get enough of the high-end shopping, cultural attractions, and elegant dining options. 

Naples Florida Marina


North Point 


For anyone needing a little pick-me-up, make a stop in the City of North Point and visit the Warm Mineral Springs. These natural springs stay 85 degrees year round and have one of the highest mineral contents in the world. Enthusiasts say the springs have healing powers.


Port Charlotte 


If you love outdoor recreation of any kind, Port Charlotte and the Charlotte Harbor are the places for you. Residents and visitors alike take advantage of the more than 165 miles of man-made waterways and Gulf of Mexico to boat, fish, swim, and more.


Sanibel Island


The small footprint, incredible amount of seashells, and laid-back lifestyle make Sanibel island the perfect one to explore on two wheels, or your own two feet. In a car, you're bound to miss out on some of the best shelling in the world, or even a sunset if you're moving too fast. 




This bustling and eclectic city on the bay is home to art of every genre. Whether you're fascinated by the world's greatest circus arts, you enjoy a well-curated museum collection, or you just love passing the time browsing independent art galleries, Sarasota is a must-visit.

Sarasota Florida Sunset 

Siesta Key 


The quintessential beach scene with water sports and nightlife is what you'll find along the 8-mile long stretch that is Siesta Key. There's something for everyone here, though, because no one can resist the shimmering quartz sand and turquoise waters. 




Whether you’re interested in historic architecture or prehistoric shark's teeth, you'll find it in this beautiful city on the Gulf. With 14 miles of beaches, excellent golf courses, and landscaped boulevards that date back to 1925, everyone in your party will find something to love.


If the appeal of Southwest Florida is too great, and you find yourself dreaming of the next time you can visit, it may be time to consider buying a home here. Medallion Home is an award-winning builder with new communities and available homes throughout Southwest Florida. If you're ready to make the move of a lifetime to Bradenton, Sarasota, or any of their surrounding communities, contact us at 914-214-9857 for locations and details. We’d love to welcome you home to Southwest Florida!