Southwest Florida Vacations
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Where to stay in Southwest Florida
Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida
North Captiva
Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.
South End
While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.
Lido Key
Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.
Central Naples
If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.
East Naples
Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.
Find the Best Southwest Florida Vacation Packages
Southwest Florida Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
₩52,617
₩88,952 total
Oct 21 - Oct 22
includes taxes & fees
9.2/10 Wonderful! (6,032 reviews)
"clean room, friendly staff, costly breakfast, didn't use the pool, sink, commode, shower arrangement not practical"
Reviewed on Sep 22, 2026
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
₩176,199
₩238,341 total
Sep 28 - Sep 29
includes taxes & fees
9.4/10 Exceptional! (2,590 reviews)
"."
Reviewed on Sep 21, 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
₩203,664
₩297,340 total
Oct 14 - Oct 15
includes taxes & fees
9.2/10 Wonderful! (3,396 reviews)
"Bueno"
Reviewed on Sep 22, 2026
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.
Stay near popular Southwest Florida attractions
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 favorite.
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.
St. Armands Circle
9.4/10 (5,556 reviews)
This elegant open-air marketplace blends upscale shopping with European charm, surrounded by historic Ringling statues. Browse over 130 boutiques and dine al fresco at sidewalk cafés overlooking Circle Park.
Photo by Michael Schuier
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 fossilized treasures along the shoreline or simply relax beneath the iconic sail-style pavilion.
Vanderbilt Beach
9.2/10 (2,388 reviews)
Vanderbilt Beach dazzles with powdery white sand and crystal-clear Gulf waters perfect for shell collecting. Arrive before sunset to witness the sky's dramatic transformation.
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.
Turtle Beach
9.0/10 (1,163 reviews)
If a restful vacation is part of your travel plans, Turtle Beach might be the perfect place to seek out during your trip to Siesta Key. Wander the seaside or discover the sunsets in this relaxing area.
Frequently asked questions
How much does a Southwest Florida vacation package cost?
Less than you might think — from just , in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your getaway to Southwest Florida is just a few clicks away.
How do I get a cheap travel package to Southwest Florida?
Browse and book everything in the one place with our Southwest Florida vacation packages. We have incredible bargains on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you'll have the flexibility to mix and match all you want.
Where should I stay in Southwest Florida?
You can't go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.
What are the top hotels in Southwest Florida?
Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travelers.
How far in advance should I book my Southwest Florida vacation?
Get rewarded with the widest variety at the cheapest prices by booking your vacation to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream vacation!
What does an Expedia Southwest Florida travel package include?
That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida vacation looks like, you're sure to save!
What should I know before booking a Southwest Florida travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.
If I'm not able to travel, can I cancel my Southwest Florida vacation package?
It's hard to predict what the future holds, so it's good to know that you can cancel or change your Southwest Florida vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
