Southwest Florida Kid friendly Vacations 2026

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Top Kid friendly vacation packages in Southwest Florida

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

Pink Shell Beach Resort and Marina

$921

per person

Nov 25 - Nov 28

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.6/10 Exceptional! (1,477 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$6,029

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Albany (ALB) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The only downside was the pool was cold and wish they heated it since there was more of a coldfront here this week.

Reviewed on Oct 21, 2026

Sundial Beach Resort & Spa

Mid Island

$2,486

per person

Dec 26 - Dec 30

found 24 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Everything was fine except the first room they gave us was with cockroaches dead like 7 or 8 but we went back to the lobby and they were very nice and change our room. The other thing that we didn’t like was the beds, they are extremely hard. Everything else was fine. Very familiar and relaxing.

Reviewed on Oct 25, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$1,569

per person

Dec 26 - Dec 28

just found

Roundtrip non-stop flight included

Burlington (BTV) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Hyatt Regency Coconut Point Resort & Spa

$2,656

per person

Dec 27 - Dec 30

just found

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9/10 Wonderful! (1,006 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

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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

$2,486

per person

Dec 26 - Dec 30

found 24 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Reviewed on Oct 25, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$6,029

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Albany (ALB) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The only downside was the pool was cold and wish they heated it since there was more of a coldfront here this week.

Reviewed on Oct 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

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

$1,209

per person

Dec 26 - Dec 29

found 5 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,707

per person

Jan 2 - Jan 5

found 23 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The only downside was the pool was cold and wish they heated it since there was more of a coldfront here this week.

Reviewed on Oct 21, 2026

Pink Shell Beach Resort and Marina

$1,823

per person

Dec 26 - Dec 29

found 5 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

9.6/10 Exceptional! (1,477 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

$1,439

per person

Dec 26 - Dec 30

found 24 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

GullWing Beach Resort

South Island

$2,059

per person

Dec 28 - Jan 1

found 24 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.4/10 Exceptional! (976 reviews)

Edison Beach House

$1,623

per person

Dec 26 - Dec 30

found 24 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.4/10 Exceptional! (1,921 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

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 $921. 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.

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! (2,717 reviews)

"Everything was fine except the first room they gave us was with cockroaches dead like 7 or 8 but we went back to the lobby and they were very nice and change our room. The other thing that we didn’t like was the beds, they are extremely hard. Everything else was fine. Very familiar and relaxing."

Reviewed on Oct 25, 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 ...

8.4/10 Very Good! (1,001 reviews)

"We weren’t notified in time to change our plans that the Captiva landing with the waterpark and other amenities would be closed for refurbishing during our stay. Otherwise, the island is quaint, quiet, and we saw plenty of wildlife. The staff was wonderful. The beach was clean with soft sand and ..."

Reviewed on Oct 23, 2026

See all 48,200 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.