A crowded beach with people sunbathing and swimming.

Southwest Florida Beach Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Beach vacation packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
  • Aug 24 - Aug 30

    The Perry Hotel Naples + Flight

    Naples
    6 nights
    4.5 star property
    9.6/10 - Exceptional (965 reviews)
    "We were early and was able to check in. They front desk employee was very pleasant and made sure we had a room with a good view, since we were celebrating a special birthday. We felt special and were very pleased with our experience. "
    Reviewed July 24, 2026
    Roundtrip Montreal (YUL) - Fort Myers (RSW)
    YUL - RSW1 stop RSW - YUL1 stop
    CA $1,706
    CA $1,104
    per traveller
    found 17 hours ago
    The Perry Hotel Naples
  • Sept 3 - Sept 8

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,002 reviews)
    "Excelent"
    Reviewed July 24, 2026
    Roundtrip Toronto (YTO) - Fort Myers (RSW)
    YYZ - RSW1 stop RSW - YYZ1 stop
    CA $2,684
    CA $1,691
    per traveller
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Sept 29 - Oct 4

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    5 nights
    3.0 star property
    9.2/10 - Wonderful (562 reviews)
    "The staff was excellent! Our accommodations were very nice, very clean and well maintained. Everything we needed was right at our fingertips during our entire stay."
    Reviewed July 23, 2026
    Roundtrip Toronto (YYZ) - Tampa (TPA)
    YYZ - TPANonstop TPA - YYZ1 stop
    CA $2,182
    CA $1,531
    per traveller
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Aug 30 - Sept 5

    Marriott Sanibel Harbour Resort & Spa + Flight

    Punta Rassa
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,002 reviews)
    Roundtrip Montreal (YMQ) - Fort Myers (RSW)
    YUL - RSW1 stop RSW - YUL1 stop
    CA $1,601
    CA $1,206
    per traveller
    found 1 day ago
    Marriott Sanibel Harbour Resort & Spa
  • Oct 1 - Oct 6

    The Westin Sarasota + Flight

    Central Sarasota
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,159 reviews)
    "Excellent location and hotel."
    Reviewed July 25, 2026
    Roundtrip Montreal (YUL) - Tampa (TPA)
    YUL - TPA1 stop TPA - YUL1 stop
    CA $1,551
    CA $1,222
    per traveller
    found 1 day ago
    The Westin Sarasota

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Top Beach Southwest Florida Hotels

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.

Find the best beach vacations in Southwest Florida

What are some benefits when booking beach vacations in Southwest Florida?

When you travel to the beach in Southwest Florida, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Southwest Florida?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Southwest Florida trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Southwest Florida?

There are quite a few things you can do to get cheap beach vacations in Southwest Florida. Prices range from CA $1,104, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Southwest Florida. These package deals let you save by booking your accommodation and your flight together with savings of up to 35.

Why should I book family beach vacations?

When you're travelling with the family to Southwest Florida, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Southwest Florida?

It's easy to find a beachfront vacation accommodation in Southwest Florida using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Southwest Florida as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Southwest Florida is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Florida. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.