Southwest Florida Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
If you're spending some time in South End, South Marco Beach and Marco Island Ski & Watersports are top sights worth seeing.
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.
Siesta Key Village
Siesta Key Village is known for its stunning beaches, and with sights like Siesta Key Beach and Siesta Key Farmers Market, you won't get bored spending a day wandering around this part of Siesta Key.
Central Naples
While visiting Central Naples, you might make a stop by sights like Naples Grande Golf Club and Naples Zoo at Caribbean Gardens.
Top hotels in Southwest Florida
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
Rp696.011
Rp1.166.383 total
25 Aug - 26 Aug
includes taxes & fees
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
Rp2.692.142
Rp3.541.976 total
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (2,509 reviews)
"Staff is always friendly and makes you feel welcomed. The entire staff goes above and beyond to accommodate and request or needs prior to arriving and upon arrival. Love the Anna Marie Island Margaritaville Compass location!"
Reviewed on 24 Aug 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
Rp2.541.992
Rp3.738.809 total
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (3,264 reviews)
"Great"
Reviewed on 24 Aug 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 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.
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.
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.
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.
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 pavement cafés overlooking Circle Park.
Coquina Beach
9.4/10 (818 reviews)
Coquina Beach dazzles with pristine white sands and turquoise waters on Anna Maria Island's southern tip. Enjoy swimming and dolphin-watching under the shade of Australian pine trees.
What to do in Southwest Florida
Palm Beach: Sightseeing Catamaran Cruise
Rp1.091.307
per adult
90% of travellers recommend
Sightseeing Hakuna Matata Catamaran Cruise in Palm Beach
Rp1.091.307
per adult
92% of travellers recommend
Frequently asked questions
How much does a Southwest Florida holiday package cost?
Less than you might think — from just , in fact! By bundling flights, hotels and car rentals into your own custom-built holiday 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 holiday 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 travellers.
How far in advance should I book my Southwest Florida holiday?
Get rewarded with the widest variety at the cheapest prices by booking your holiday 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 holiday!
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 holiday 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 holiday is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia holiday 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 holiday 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 holiday 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
