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
The price is ₩78,889 per night from Aug 10 to Aug 11
₩78,889
₩105,759 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (4,217 reviews)
"Clean, cute, would have preferred private bathroom/shower"

Reviewed on Aug 4, 2025

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 ₩226,177 per night from Sep 1 to Sep 2
₩226,177
₩312,585 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,648 reviews)
"Mucho ruido parecia que estaban remodelando en la instalacion o su alrededor"

Reviewed on Aug 3, 2025

Naples Grande Beach Resort
The Westin Sarasota

The Westin Sarasota

4 out of 5
100 Marina View Drive, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is ₩248,051 per night from Aug 10 to Aug 11
₩248,051
₩314,748 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,049 reviews)
"Easy to navigate and hotel takes you to Lido beach where you can rent chairs/umbrellas and have access to food. You can Uber to Siesta beach and order drinks and food from your chair at the beach. I love that!"

Reviewed on Aug 4, 2025

The Westin Sarasota
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

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

4.5/5(1,425 reviews)

The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

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

Fifth Avenue South

4.5/5(45 reviews)

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
Bonita Springs Public Beach

Bonita Springs Public Beach

4.5/5(594 reviews)

Why not spend a carefree afternoon at Bonita Springs Public Beach during your travels in Bonita Springs? Make time to visit the area's shops, or simply enjoy its top-notch restaurants.

Bonita Springs Public Beach

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.