Title: Luxury Vacations in Legacy Trail 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248621532652531/b53c8085-7aee-4fdc-9b51-be3d20bd1a7b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Legacy Trail Luxury Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 ## Flight and Luxury hotel deals in Legacy Trail Price found within the past 48 hours. Click for updated prices. ![The Hotel Zamora](https://images.trvl-media.com/lodging/8000000/7290000/7282700/7282620/f7a1a1af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hotel Zamora CA $1,373 per person Feb 5 - Feb 12 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 8.6/10 Excellent! (203 reviews) One of a kind, lovely staff, beautiful hotel, perfect pool area, great waterfront views. I will be back! Reviewed on Dec 3, 2025 ![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/8b0dc5d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Compass Hotel by Margaritaville Anna Maria Sound CA $1,378 per person Feb 5 - Feb 12 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Sarasota (SRQ) 9.4/10 Exceptional! (1,843 reviews) Everything was wonderful Reviewed on Dec 4, 2025 ![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Avalon Club CA $1,852 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available. Reviewed on Nov 26, 2025 ![Wyndham Grand Clearwater Beach](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Clearwater Beach CA $1,875 per person Feb 5 - Feb 12 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (2,803 reviews) It is beyond expectation, the gulf view is amazing Reviewed on Dec 4, 2025 ![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/80dcbca1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Legacy Hotel at IMG Academy CA $1,754 per person Feb 5 - Feb 12 found 24 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Sarasota (SRQ) 9/10 Wonderful! (913 reviews) HVAC was very loud. I was surprised with a resort fee. This was not disclosed on Expedia Not fair I deserve a refund of $56 Reviewed on Nov 20, 2025 Don't see what you're looking for? See all available trips from Des Moines to Legacy Trail [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Legacy Trail Price found within the past 48 hours. Click for updated prices. ![The Adaline](https://images.trvl-media.com/lodging/97000000/96050000/96044100/96044015/2cb71c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Adaline Hyde Park CA $1,289 per person Jan 7 - Jan 11 found 1 day ago Roundtrip flight included Ottawa (YOW) to Sarasota (SRQ) 9.6/10 Exceptional! (53 reviews) Very cute place! Feels like home. It’s in a walkable area really close to a lot of stores and food options. I enjoyed staying here! Reviewed on Dec 1, 2025 ![The Gemma by Brightwild](https://images.trvl-media.com/lodging/105000000/104290000/104287800/104287738/79e8e064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gemma by Brightwild CA $5,962 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 10/10 Exceptional! (2 reviews) ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Longboat Key Resort CA $5,140 per person Jan 26 - Jan 31 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) to Sarasota (SRQ) 9.8/10 Exceptional! (56 reviews) Everything was new, clean and the service was amazing! The best part is how many activities there are for kids. This is perfect for families to enjoy and relax! We'll be back very soon! Reviewed on Dec 4, 2025 Don't see what you're looking for? See all available trips from Des Moines to Legacy Trail [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Legacy Trail Price found within the past 48 hours. Click for updated prices. ![Wyndham Grand Clearwater Beach](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Clearwater Beach CA $943 per person Feb 22 - Feb 25 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (2,803 reviews) It is beyond expectation, the gulf view is amazing Reviewed on Dec 4, 2025 ![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Avalon Club CA $1,387 per person Feb 22 - Feb 25 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available. Reviewed on Nov 26, 2025 ![The Gemma by Brightwild](https://images.trvl-media.com/lodging/105000000/104290000/104287800/104287738/79e8e064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gemma by Brightwild CA $3,530 per person Feb 22 - Feb 25 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 10/10 Exceptional! (2 reviews) Don't see what you're looking for? See all available trips from Des Moines to Legacy Trail [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Legacy Trail Price found within the past 48 hours. Click for updated prices. ![Wyndham Grand Clearwater Beach](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Clearwater Beach CA $1,234 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (2,803 reviews) It is beyond expectation, the gulf view is amazing Reviewed on Dec 4, 2025 ![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Avalon Club CA $1,852 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available. Reviewed on Nov 26, 2025 ![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/0a89d66d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cedar Cove Resort and Cottages CA $1,268 per person Jan 9 - Jan 13 found 22 hours ago Roundtrip flight included Toronto (YYZ) to Sarasota (SRQ) 9.2/10 Wonderful! (480 reviews) Perfect location. Nice clean comfortable room. I will come back Reviewed on Oct 28, 2025 Don't see what you're looking for? See all available trips from Des Moines to Legacy Trail [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Legacy Trail vacation with Expedia #### 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 $943, 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 38\. 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Flights to Legacy Trail ](https://expedia.ca/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[ Legacy Trail Hotels ](https://expedia.ca/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[ Legacy Trail Vacation Rentals ](https://expedia.ca/Legacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[ Legacy Trail Car Rentals ](https://expedia.ca/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide)[ Legacy Trail Vacations ](https://expedia.ca/Legacy-Trail.d553248621532652531.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app