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Discover the most popular places to visit in Southwest Florida
Siesta Key Beach
9.6/10 (4,113 reviews)
Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favourite.
Lido Beach
9.4/10 (6,329 reviews)
Lido Beach enchants with pristine white sands and calm waters along Sarasota's coast. Spend the day swimming in crystal-clear waters before strolling to nearby St. Armands Circle for upscale dining.
Naples Beach
9.4/10 (6,040 reviews)
Pristine white sands and clear Gulf waters frame the historic Naples Pier, stretching 1,000 feet into the sea. Watch for dolphins while enjoying panoramic sunset views from this quintessential Florida beach.
Venice Beach
9.2/10 (2,687 reviews)
Known as the "Shark Tooth Capital of the World," Venice Beach offers pristine sands and clear Gulf waters. Search for fossilised treasures along the shoreline or simply relax beneath the iconic sail-style pavilion.
Fifth Avenue South
9.4/10 (2,799 reviews)
Fifth Avenue South pulses as Naples' elegant heart, lined with upscale boutiques and art galleries. Stroll beneath swaying palms and enjoy ambient lighting and outdoor dining when the avenue truly comes alive.
"It was a beautiful property. Small but appropriate fenced area for our dog. Pool was nice. Host was friendly and available lf we needed her. We really enjoyed our stay. "
"The apartment was amazing and the perfect location for anyone visiting Sarasota. It was just the perfect place downtown and just 10min drive away to lido Key. Christie was an excellent host and made sure we had everything we needed for the stay. It was very clean and the perfect for the occasion. Large bedroom and a spacey living room. I recommend anyone staying here!"
"Our family of 4 Adults and 3 kids just stayed and had a wonderful week! The kids loved all the amenities, and they had everything we needed for our 8 month old! We come yearly fo vacation and will be getting this house again! "
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
How can I book the best ski holiday to Southwest Florida in 2026/2027?
Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Southwest Florida. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.
How can I find cheap Southwest Florida ski holidays?
Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Southwest Florida accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from . Prices and availability are subject to change. Additional terms may apply.
Can I book last-minute ski holidays to Southwest Florida?
Use our handy last-minute deals page to look for ski holidays to Southwest Florida at a steal. If your dates are fixed, simply input the details and see what specials are available.
What should I consider when booking family ski holidays in Southwest Florida?
Southwest Florida is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.
Can I book all-inclusive ski holidays to Southwest Florida?
All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Southwest Florida. If not, consider booking your flights and accommodation together to save money that way instead.
When's the best time of year to plan a ski trip to Southwest Florida?
Ski season in Southwest Florida generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.
How can I find the best deals on Southwest Florida ski holiday packages?
If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.
Can I book a Southwest Florida ski trip with free cancellation and/or flexible dates?
If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Southwest Florida that offer it.
Why should I book a ski holiday package in Southwest Florida with Expedia?
Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.