Southwest Florida Kid friendly Vacations

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Flight and Kid friendly hotel deals in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

CA $960
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,417 reviews)
Breakfast was off the chain. Buffet as well as made to order eggs or omelets. Staff was extremely helpful and friendly The restaurants there were 5 star quality. Be careful of the curbs around the buildings and parking, they are various heights and can easily be misjudged. Other than that, had an awesome time. Will return. :). Dbt

Reviewed on Aug 14, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $1,190
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Fort Myers (RSW)
8.6/10 Excellent! (1,012 reviews)
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
CA $3,572
per person
Oct 24 - Oct 29
found 15 hours ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.6/10 Exceptional! (28 reviews)
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
CA $1,669
per person
Sep 30 - Oct 4
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (2,680 reviews)
Great place

Reviewed on Aug 14, 2026

Hyatt Regency Coconut Point Resort & Spa

Hyatt Regency Coconut Point Resort & Spa

CA $2,557
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
The staff

Reviewed on Aug 14, 2026

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5* Kid friendly holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
CA $1,669
per person
Sep 30 - Oct 4
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (2,680 reviews)
Great place

Reviewed on Aug 14, 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
CA $3,572
per person
Oct 24 - Oct 29
found 15 hours ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.6/10 Exceptional! (28 reviews)
Don't see what you're looking for?
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3 Night Kid friendly holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $831
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,012 reviews)
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

CA $960
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,417 reviews)
Breakfast was off the chain. Buffet as well as made to order eggs or omelets. Staff was extremely helpful and friendly The restaurants there were 5 star quality. Be careful of the curbs around the buildings and parking, they are various heights and can easily be misjudged. Other than that, had an awesome time. Will return. :). Dbt

Reviewed on Aug 14, 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
CA $2,665
per person
Oct 2 - Oct 5
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (28 reviews)
Don't see what you're looking for?
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4 Night Kid friendly holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $868
per person
Sep 20 - Sep 24
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,012 reviews)
South Seas

South Seas

CA $1,209
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Fort Myers (RSW)
8.4/10 Very good! (1,004 reviews)
We had a wonderful stay at South Seas Resort! Everything was perfect from beginning to end. The staff was very friendly, helpful, and attentive, and the entire resort was extremely clean, well maintained and organize. The location is beautiful, and the water park for the kids was absolutely excellent, they all had a great time! Everything was very family-friendly and made our stay relaxing and enjoyable. I would definitely recommend Southseas Resort to families and anyone looking for a clean, comfortable and fun place to stay .

Reviewed on Aug 13, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

CA $1,268
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
Was able to watch the dolphins in the morning from the balcony. Short walk across the street to the beach and they have umbrellas and chairs to rent. Would definitely come back.

Reviewed on Aug 13, 2026

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Plan the perfect family-friendly vacation in Southwest Florida with Expedia

What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Southwest Florida are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Southwest Florida.

Are there cheap family vacations to Southwest Florida?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Southwest Florida depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

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

Yes, you'll find plenty of all-inclusive family vacation packages for Southwest Florida. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Southwest Florida, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Southwest Florida or something a bit more relaxed.

Can I find luxury family vacations in Southwest Florida?

If you're looking for a luxury family vacation to Southwest Florida, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Southwest Florida.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Southwest Florida are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

Kid friendly Hotels in Southwest Florida

Pink Shell Beach Resort and Marina

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! (1,425 reviews)
"Breakfast was off the chain. Buffet as well as made to order eggs or omelets. Staff was extremely helpful and friendly The restaurants there were 5 star quality. Be careful of the curbs around the buildings and parking, they are various heights and can easily be misjudged. Other than that, had an ..."

Reviewed on Aug 14, 2026

Pink Shell Beach Resort and Marina
Sundial Beach Resort & Spa

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! (2,685 reviews)
"Great place"

Reviewed on Aug 14, 2026

Sundial Beach Resort & Spa
South Seas

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 Bowman's Beach and Jungle Drums are ...
8.4/10 Very good! (1,001 reviews)
"We had a wonderful stay at South Seas Resort! Everything was perfect from beginning to end. The staff was very friendly, helpful, and attentive, and the entire resort was extremely clean, well maintained and organize. The location is beautiful, and the water park for the kids was absolutely excellent, ..."

Reviewed on Aug 13, 2026

South Seas
See all 47,330 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.

Things to do

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

CA $86
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Craft Beer and Wine Sunset Cruise in Palm Beach

Craft Beer and Wine Sunset Cruise in Palm Beach

CA $83
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Green sea turtle swimming by the snorkel trail

Guided Snorkel Tour Phil Foster Park (HIGH TIDE ONLY-FREE VIDEOS)

CA $106
per adult
100% of travellers recommend
Guided Snorkel Tour Phil Foster Park (HIGH TIDE ONLY-FREE VIDEOS)
See all activities in Southwest Florida

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.