Southwest Florida Kid friendly Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 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

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

$413

per person

Nov 17 - Nov 19

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

All anybody wants is tips. Food was expensive and not good. And when you get home they change you again for resort fees. Horrible

Reviewed on Oct 17, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$1,287

per person

Nov 17 - Nov 19

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) 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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$681

per person

Dec 18 - Dec 20

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Sundial Beach Resort & Spa

Mid Island

$597

per person

Nov 17 - Nov 19

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Gotta get rid of the sand chiggers.

Reviewed on Oct 17, 2026

Hyatt Regency Coconut Point Resort & Spa

$1,271

per person

Dec 19 - Dec 22

found 20 hours ago

Roundtrip flight included

New York (JFK) 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

View all trips

5* Kid friendly vacations in Southwest Florida

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

Sundial Beach Resort & Spa

Mid Island

$597

per person

Nov 17 - Nov 19

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Gotta get rid of the sand chiggers.

Reviewed on Oct 17, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$1,287

per person

Nov 17 - Nov 19

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) 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

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

$790

per person

Dec 18 - Dec 21

found 14 hours ago

Roundtrip flight included

Lansing (LAN) 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

$2,044

per person

Jan 8 - Jan 11

found 13 hours ago

Roundtrip flight included

Philadelphia (PHL) 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

Sundial Beach Resort & Spa

Mid Island

$1,078

per person

Dec 18 - Dec 21

found 14 hours ago

Roundtrip flight included

Lansing (LAN) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Gotta get rid of the sand chiggers.

Reviewed on Oct 17, 2026

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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$676

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

GullWing Beach Resort

South Island

$1,167

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MKC) to Fort Myers (RSW)

9.4/10 Exceptional! (976 reviews)

Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities.

Reviewed on Oct 17, 2026

Edison Beach House

$793

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MKC) 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 $413. 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 ...

9.4/10 Exceptional! (1,480 reviews)

"All anybody wants is tips. Food was expensive and not good. And when you get home they change you again for resort fees. Horrible"

Reviewed on Oct 17, 2026

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! (2,716 reviews)

"Gotta get rid of the sand chiggers."

Reviewed on Oct 17, 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.