Southwest Florida Trips (flight + hotel)

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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

Top hotels in Southwest Florida

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! (4,220 reviews)
"Beautiful decor and boutique setting"

Reviewed on Aug 8, 2025

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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 P8,651 per night from Sep 7 to Sep 8
P8,651
P12,137 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,660 reviews)
"Loved the convenience of the rides to and from the beach. The food at the restaurants was great and staff offered great service. We will definitely be back!!!"

Reviewed on Aug 6, 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 P10,220 per night from Aug 17 to Aug 18
P10,220
P12,968 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,051 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 43,657 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.

Popular places to visit

Lido 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
St. Armands Circle showing a statue or sculpture

St. Armands Circle

Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.

St. Armands Circle
Naples Pier showing landscape views and a beach as well as a large group of people

Naples Pier

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

What to do in Southwest Florida

Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

P2,975
per adult
92% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

P6,397
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
Flamingle Happy Hour Cruise

Flamingle Happy Hour Cruise

P2,353
per adult
Flamingle Happy Hour Cruise
See all activities in Southwest Florida

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.