Southwest Florida Kid friendly Vacations 2026

Top Kid friendly vacation packages in Southwest Florida

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$517

per person

Nov 15 - Nov 18

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

I love everything about this hotel

Reviewed on Oct 13, 2026

Sundial Beach Resort & Spa

Mid Island

$1,114

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

The room was clean but pretty bare for a condo u it. The bed we had has pretty hard. The couch was stiff as a board. The bathroom only had one sink and the only mirror in the whole place. The Staff were great. Beach view was great. Only ate breakfast once at the restaurant and it was not that good and very expensive. Should have know it was not as good as we were the only ones in there.

Reviewed on Oct 15, 2026

Pink Shell Beach Resort and Marina

$939

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,141

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This was our first time at Four Seasons and I might say it will not be our last. Everything was amazing, The staff throughout were excellent.

Reviewed on Oct 12, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,139

per person

Dec 17 - Dec 20

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,006 reviews)

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5* Kid friendly vacations in Southwest Florida

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

Sundial Beach Resort & Spa

Mid Island

$1,114

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Reviewed on Oct 15, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,141

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This was our first time at Four Seasons and I might say it will not be our last. Everything was amazing, The staff throughout were excellent.

Reviewed on Oct 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

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3 Night Kid friendly vacations in Southwest Florida

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$517

per person

Nov 15 - Nov 18

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

I love everything about this hotel

Reviewed on Oct 13, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,352

per person

Dec 17 - Dec 20

found 20 hours ago

Roundtrip flight included

Columbus (CMH) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This was our first time at Four Seasons and I might say it will not be our last. Everything was amazing, The staff throughout were excellent.

Reviewed on Oct 12, 2026

Pink Shell Beach Resort and Marina

$839

per person

Dec 17 - Dec 20

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

4 Night Kid friendly vacations in Southwest Florida

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$579

per person

Nov 15 - Nov 19

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

I love everything about this hotel

Reviewed on Oct 13, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$729

per person

Nov 16 - Nov 20

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Edison Beach House

$771

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) to Fort Myers (RSW)

9.4/10 Exceptional! (1,921 reviews)

Everything was good,no complains.

Reviewed on Oct 16, 2026

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How can I find the best family vacation packages in Southwest Florida?

For fam-tastic vacation packages in Southwest Florida, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Southwest Florida on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Southwest Florida cost?

You could book your amazing family trip to Southwest Florida just $517. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

When is the best time of year for family vacations to Southwest Florida?

If you’re crowd-cautious, the quieter months of are positively perfect in Southwest Florida. But it’s if you’d rather mingle with the masses. Match your wardrobe to the weather and it’s always a wonderful time to visit Southwest Florida.

Can I book an all-inclusive Southwest Florida family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Southwest Florida?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Southwest Florida family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Southwest Florida landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Southwest Florida family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Southwest Florida family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Southwest Florida Hotels

Pink Shell Beach Resort and Marina

275 Estero Blvd Fort Myers Beach FL

2 hours drive from Siesta Key Beach

Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the ...

Sundial Beach Resort & Spa

1451 Middle Gulf Drive Sanibel FL

2 hours drive from Siesta Key Beach

Book a stay at this luxury aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the property condition in our reviews. ...

8.6/10 Excellent! (2,715 reviews)

"The room was clean but pretty bare for a condo u it. The bed we had has pretty hard. The couch was stiff as a board. The bathroom only had one sink and the only mirror in the whole place. The Staff were great. Beach view was great. Only ate breakfast once at the restaurant and it was not that good ..."

Reviewed on Oct 15, 2026

South Seas

5400 South Seas Plantation Rd Captiva FL

2 hours drive from Siesta Key Beach

Book a stay at this beach resort in Captiva. Enjoy 6 outdoor pools, 5 restaurants, and a private beach. Popular attractions McCarthy's Marina and Captiva Chapel ...

See all 47,930 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.