Luxury Vacations in Legacy Trail 2026

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Flight and Luxury hotel deals in Legacy Trail

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

CW Resort

Save 100% on your flight

CA $1,461

per person

Nov 26 - Dec 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Incredible place to stay.highly recommended.

Reviewed on Oct 6, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $1,696

per person

Nov 26 - Dec 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The Hotel Zamora

Save 100% on your flight

CA $1,658

per person

Dec 23 - Dec 29

found 7 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

8.8/10 Excellent! (423 reviews)

The Avalon Club

Save 100% on your flight

CA $2,947

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

The Westin Sarasota

Central Sarasota

CA $1,757

per person

Nov 23 - Nov 29

found 22 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Tampa (TPA)

9.2/10 Wonderful! (1,178 reviews)

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5* Luxury holidays in Legacy Trail

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

The Ritz-Carlton, Sarasota

Central Sarasota

CA $2,216

per person

Nov 13 - Nov 16

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.2/10 Wonderful! (1,024 reviews)

The St. Regis Longboat Key Resort

CA $4,287

per person

Nov 13 - Nov 16

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.8/10 Exceptional! (97 reviews)

The Gemma by Brightwild

CA $3,294

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.8/10 Exceptional! (7 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

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3 Night Luxury holidays in Legacy Trail

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

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $897

per person

Nov 5 - Nov 8

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The Avalon Club

Save 100% on your flight

CA $2,947

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

CW Resort

CA $1,940

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Incredible place to stay.highly recommended.

Reviewed on Oct 6, 2026

Don't see what you're looking for?

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4 Night Luxury holidays in Legacy Trail

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

CW Resort

Save 100% on your flight

CA $975

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Incredible place to stay.highly recommended.

Reviewed on Oct 6, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

CA $1,195

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $1,073

per person

Nov 20 - Nov 24

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

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What are some benefits when booking luxury Legacy Trail vacations?

When you book a luxury Legacy Trail vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Legacy Trail?

If you're looking for something luxurious in Legacy Trail, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $897, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 35. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Legacy Trail. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Legacy Trail?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Legacy Trail.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Legacy Trail. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Legacy Trail?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Legacy Trail or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Legacy Trail. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.