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
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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.

Find hotels in North Captiva

Find the Best Southwest Florida Vacation Packages

Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,204 reviews)
"I spent 2 nights here with my best friend for a birthday getaway and it exceeded our expectations. Every aspect of our stay was a 10 +! The front desk & housekeeping were all smiles at every interaction! Would most definitely recommend and I would stay there again if I am back in the area."

Reviewed on 2025/7/30

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Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
The price is NT$4,892 per night from Sep 1 to Sep 2
NT$4,892
NT$6,761 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,637 reviews)
"Great experience"

Reviewed on 2025/8/1

Naples Grande Beach Resort
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is NT$5,356 per night from Aug 16 to Aug 17
NT$5,356
NT$7,307 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (1,275 reviews)
"Everything was amazing about this hotel until our shower started to overflow and they were in our room until 130a trying to fix it and couldnt. They did accommodate us to a different which our keys continued to fail at the door. I felt like they could have accommodated alot more for all the ..."

Reviewed on 2025/7/31

Sunseeker Resort Charlotte Harbor
See all 43,487 properties in Southwest Florida
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.

Discover the most popular places to visit in Southwest Florida

Lido Beach showing general coastal views and a sandy beach

Lido Beach

Nothing says vacation like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.

Lido Beach
Turtle Beach

Turtle Beach

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.

Turtle Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.