Beach Vacations in Southwest Florida 2026

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Flight and Beach hotel deals in Southwest Florida

Price found within the past 48 hours. Click for updated prices.

Inn at Pelican Bay

Pelican Bay

CA $1,162

per person

Oct 15 - Oct 19

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (1,004 reviews)

Such a beautiful boutique inn. My boyfriend and I enjoyed being here. We had a gorgeous lake view king room. Highly recommend.

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

CA $5,235

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Outstanding massage

Reviewed on Sep 1, 2026

Sundial Beach Resort & Spa

Mid Island

CA $1,563

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

We booked with a 3rd party , the web pics showed a balcony. Are room had now balcony. Went to Terry Manager was accommodating although he stated the pics from a 3rd party was on 3rd party web not on the resorts web. Needless to say every was very clean the tiki bar staff very sweet. Be warned iof the sand flees u can not see them and they will eat u alive

Reviewed on Sep 12, 2026

Pink Shell Beach Resort and Marina

CA $1,201

per person

Dec 6 - Dec 11

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9.4/10 Exceptional! (1,447 reviews)

Hilton Marco Island Beach Resort and Spa

South End

CA $1,853

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Fort Myers (RSW)

9/10 Wonderful! (2,004 reviews)

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5* Beach holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.

Sundial Beach Resort & Spa

Mid Island

CA $1,563

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

CA $5,235

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Outstanding massage

Reviewed on Sep 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

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4 Night Beach holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.

Tropical Beach Resorts

South Village

CA $897

per person

Nov 5 - Nov 9

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (5,824 reviews)

Casey Key Resorts - Beachfront

CA $1,163

per person

Nov 14 - Nov 18

found 23 hours ago

Roundtrip flight included

Montreal (YMQ) to Sarasota (SRQ)

8.8/10 Excellent! (1,002 reviews)

Great place to stay and enjoy a relaxing vacation.

Reviewed on Aug 28, 2026

Inn at the Beach

Venice Island

CA $1,093

per person

Nov 14 - Nov 18

found 23 hours ago

Roundtrip flight included

Montreal (YMQ) to Fort Myers (RSW)

9.8/10 Exceptional! (1,053 reviews)

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See all available trips from Columbus to Southwest Florida

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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 $897, 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 17.

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.

Beach Hotels in Southwest Florida

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

41 min drive from Siesta Key Beach

Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

9.4/10 Exceptional! (2,551 reviews)

"My only negative comment is the noseeums bug bites in the property. Bring your own bug spray.. otherwise beautiful place ‼️"

Reviewed on Sep 12, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

11800 Coconut Cove Drive Bonita Springs FL

2 hours drive from Siesta Key Beach

Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Bonita Springs Public Beach and Hertz ...

Marriott Sanibel Harbour Resort & Spa

17260 Harbour Pointe Dr Fort Myers FL

2 hours drive from Siesta Key Beach

Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...

See all 47,311 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.