Kid friendly Vacations in Legacy Trail 2026

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Flight and Kid friendly hotel deals in Legacy Trail

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

The Westin Sarasota

Central Sarasota

CA $705

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

The Hotel Zamora

CA $1,654

per person

Nov 8 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

8.8/10 Excellent! (388 reviews)

The hotel is beautiful and very clean. Great amenities, close to great restaurants and beautiful stretch of the beach. Lovely service, staff weee friendly and very helpful. Rachel at the hotel restaurant was amazing. We had a beautiful weekend. Will definitely visit again.

Reviewed on Aug 21, 2026

Island Grand at TradeWinds

CA $1,917

per person

Oct 24 - Oct 31

found 4 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Tampa (TPA)

7.8/10 Good! (1,322 reviews)

This hotel is old and the rooms a bit musty. There is still only one elevator working. There is a new portion of the property called The Hall. Overall restaurants were pretty good but prices very high. Most of the amenities were available to use due to weather which was unfortunate bc we booked specifically for the water park on the ocean. I asked For a blow dryer and the man that brought it, walked right past my husband into our bathroom INSISTING we had one. We did not. The pools are small. The beach is pretty but if you want an extra umbrella it’s $30 extra a day. The woman that checked us in was quite rude. They expect a tip for everything. Buy a can of beer and bring it up to the register…tip for the cashier checking us out. The motto is just let go. I say Just don’t go. This trip easily cost us as much as a five star all inclusive in Mexico.

Reviewed on Aug 24, 2026

The Don CeSar

CA $2,755

per person

Oct 24 - Oct 31

found 4 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Tampa (TPA)

9/10 Wonderful! (1,283 reviews)

Excellent service. Very clean. Our favorite place!

Reviewed on Aug 23, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,161

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

9.6/10 Exceptional! (1,165 reviews)

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5* Kid friendly holidays in Legacy Trail

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

Little Harbor Resort at Bahia Beach

CA $1,007

per person

Sep 24 - Sep 29

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (27 reviews)

Loved the rental. Quiet neighbors.

Reviewed on Apr 27, 2026

The Gemma by Brightwild

CA $4,171

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

The Tampa EDITION

Downtown Tampa

CA $1,235

per person

Oct 31 - Nov 3

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (410 reviews)

Beautiful green plants and elegant décor create a warm and relaxing atmosphere. The customer service was excellent, and the staff were friendly and attentive. Overall, a wonderful hotel experience!

Reviewed on Aug 20, 2026

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3 Night Kid friendly holidays in Legacy Trail

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

The Hotel Zamora

CA $738

per person

Oct 31 - Nov 3

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

8.8/10 Excellent! (388 reviews)

Reviewed on Aug 21, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $872

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.6/10 Exceptional! (1,165 reviews)

CW Resort

CA $1,089

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

9.6/10 Exceptional! (99 reviews)

Todo nos gustó excelente propiedad

Reviewed on Aug 24, 2026

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4 Night Kid friendly holidays in Legacy Trail

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

The Fold Hotels Indian Shores

CA $628

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.2/10 Wonderful! (1,006 reviews)

Amazing place! Super clean and everyone super friendly and nice

Reviewed on Aug 23, 2026

Hibiscus Suites - Gateway to Siesta Key

CA $791

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

8.6/10 Excellent! (2,412 reviews)

Good place to stay and convince

Reviewed on Aug 24, 2026

The Hotel Zamora

CA $816

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

8.8/10 Excellent! (388 reviews)

Reviewed on Aug 21, 2026

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

Whether it's luxurious or cheap, family vacations in Legacy Trail 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 Legacy Trail.

Are there cheap family vacations to Legacy Trail?

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 Legacy Trail 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 Legacy Trail?

Yes, you'll find plenty of all-inclusive family vacation packages for Legacy Trail. 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 Legacy Trail, 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 Legacy Trail or something a bit more relaxed.

Can I find luxury family vacations in Legacy Trail?

If you're looking for a luxury family vacation to Legacy Trail, 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 Legacy Trail.

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 Legacy Trail 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.