A crowded beach with people sunbathing and swimming.

Southwest Florida Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Southwest Florida Vacation

Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize 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 vacation to the second you come back home, Expedia has you covered each step of the way.

The Latest Southwest Florida Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 18 - Jan 21

    Pelican Grand Beach Resort - A Noble House Resort + Flight

    East Fort Lauderdale
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,807 reviews)
    Roundtrip • Ottawa (YOW) - Miami (MIA)
    YOW - MIA • Nonstop MIA - YOW • Nonstop
    Save 100% on your flight
    CA $2,355
    CA $1,340
    per traveller
    found 1 day ago
    Pelican Grand Beach Resort - A Noble House Resort
  • Feb 1 - Feb 4

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    3 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - FLL • 1 stop FLL - YUL • 1 stop
    CA $15,294
    CA $7,329
    per traveller
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • Jan 20 - Jan 25

    YotelPad Miami + Flight

    Downtown Miami
    5 nights
    4.0 star property
    8.4/10 - Very good (557 reviews)
    "Love this hotel."
    Reviewed November 7, 2026
    Roundtrip • Ottawa (YOW) - Miami (MIA)
    YOW - MIA • 1 stop MIA - YOW • Nonstop
    CA $2,499
    CA $1,409
    per traveller
    found 1 day ago
    YotelPad Miami
  • Dec 29 - Jan 4

    President Hotel Villa + Flight

    South Beach
    6 nights
    3.5 star property
    8.2/10 - Very good (1,002 reviews)
    "Good stay for a night"
    Reviewed November 3, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $3,408
    CA $1,943
    per traveller
    found 1 day ago
    President Hotel Villa
  • Dec 15 - Dec 21

    EAST Miami Residences + Flight

    Brickell
    6 nights
    5.0 star property
    9.2/10 - Wonderful (170 reviews)
    Roundtrip • Toronto (YTO) - Miami (MIA)
    YYZ - FLL • 1 stop FLL - YYZ • Nonstop
    Save 100% on your flight
    CA $4,816
    CA $2,757
    per traveller
    found 1 day ago
    EAST Miami Residences

Discover the most popular places to visit in Southwest Florida

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Southwest Florida Hotel Deals

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.

Frequently Asked Questions

How much does a Southwest Florida vacation package cost?

Less than you might think — from just CA $1,340, 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.