Southwest Florida Holidays

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Your Southwest Florida Holiday

Set off on your next big adventure with a Southwest Florida holiday package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customise your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida holiday to the second you come back home, Expedia has you covered each step of the way.

Our guide on 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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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.

Find hotels in Siesta Key Village

Southwest Florida Holiday

Southwest Florida Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tampa Intl. Airport (TPA)
Top Sights
Siesta Key Beach, Lido Beach and Honeymoon Island State Park

Our pick of the best Southwest Florida Hotel Deals

Lani Kai Beachfront Resort
Lani Kai Beachfront Resort
3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
The price is AU$322 per night from 29 June to 30 June
AU$322
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (1,016 reviews)
"The view, the room was very clean and comfortable. Even though there was still construction on the roof, the noise was not during sleep time so was happy with everything."

Reviewed on 22 Jun. 2025

Lani Kai Beachfront Resort
Compass Hotel by Margaritaville Anna Maria Sound
Compass Hotel by Margaritaville Anna Maria Sound
4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is AU$345 per night from 2 July to 3 July
AU$345
2 July - 3 July
includes taxes & fees
9.4/10 Exceptional! (1,508 reviews)
"Close to Anna Maria Island Convenient. The onsite dinner was excellent, so was the breakfast (included). Great place"

Reviewed on 23 Jun. 2025

Compass Hotel by Margaritaville Anna Maria Sound
Naples Grande Beach Resort
Naples Grande Beach Resort
4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
The price is AU$524 per night from 2 July to 3 July
AU$524
2 July - 3 July
includes taxes & fees
9/10 Wonderful! (1,534 reviews)
"The beach access and pool were fantastic! We really lived the adults only pool!"

Reviewed on 22 Jun. 2025

Naples Grande Beach Resort
See all 43,110 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.

Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

Siesta Key Beach

4/5(1 review)

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
Lido Beach

Lido Beach

Nothing says holiday 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 which includes 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

What to do in Southwest Florida

Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

AU$169
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

AU$79
per adult
94% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Guided Snorkel Experience, Free Videos in West Palm Beach

Guided Snorkel Experience, Free Videos in West Palm Beach

AU$69
per adult
Guided Snorkel Experience, Free Videos in West Palm Beach
See all activities in Southwest Florida
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.