Highland Meadows Vacation Packages

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Top Holiday Package Deals in Highland Meadows

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

Seasons Florida Resort

2 out of 5
Price was CA $1,165, price is now CA $743 per person
CA $743
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (3,629 reviews)
This is a nice hotel. I wanted a place that was quiet. The staff was great from the time I checked in until I checked out. I was very impressed at how nice the place looked nad was. Everything was where it was supposed to be. . I was impressed with the place nad I know if given the chance I would go back.

Reviewed on Jun 21, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,736, price is now CA $1,060 per person
CA $1,060
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (6,626 reviews)
We had a wonderful stay at Westgate Resort. The room was clean, comfortable, and well-maintained. The staff was friendly and helpful throughout our visit, and the property itself was beautiful and family-friendly. We especially enjoyed the amenities and overall atmosphere. The only suggestions I would make are that guests should be informed more clearly at check-in that access to the water park and certain resort amenities requires an additional fee, as this was not fully explained beforehand. Also, the $50 deposit refund has taken longer than expected to be returned. Overall, despite these minor inconveniences, we had a great experience and would definitely stay here again. The resort offers excellent accommodations and a pleasant environment for families and travelers alike.

Reviewed on Jun 20, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,844, price is now CA $1,765 per person
CA $1,765
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (550 reviews)
Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien.

Reviewed on May 25, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,917, price is now CA $1,927 per person
CA $1,927
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,009 reviews)
The cottage was wonderful. Stocked with everything you need just bring your food, drink and toilet paper! The cottage we stayed at was a perfect location just 5 minute walk to the amazing pool complex. The resort is great. Planning on going back soon.

Reviewed on Jun 20, 2026

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Price was CA $1,376, price is now CA $930 per person
CA $930
per person
Aug 30 - Sep 6
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (1,881 reviews)
We live in Cocoa, in DB for medical apptmts. Great view from oceanfront suite. We did not use any amenities - pool was busy. The staff was helpful. One young man from Jamaica (he was new) went above and beyond to find a small missing tote bag. The food at Oasis (outdoor bar/grill at Fountain Hotel, next door, short walk) was very good. We ate there a few times, good every visit.

Reviewed on Jun 21, 2026

Where to stay in Highland Meadows

Find the best Highland Meadows areas and neighborhoods for the activities you enjoy most. Learn more about Highland Meadows
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Watersong

4/5(1 area review)

Watersong might not have many top sights, but Providence Golf Club and Reunion Resort Golf Course are two attractions nearby that you can check out.

Find hotels in Watersong

Highland Meadows Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 6 to Jul 7
CA $215
CA $242 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (5,844 reviews)
"Very nice Clean room. Close to.pool"

Reviewed on Jun 21, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is CA $282 per night from Jun 22 to Jun 23
CA $282
CA $395 total
Jun 22 - Jun 23
includes taxes & fees
8/10 Very Good! (10,233 reviews)
"Abitaciones muy amplias la pasamos bien volveria"

Reviewed on Jun 21, 2026

The Grove Resort & Water Park Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $47 per night from Jun 24 to Jun 25
CA $47
CA $116 total
Jun 24 - Jun 25
includes taxes & fees
9.4/10 Exceptional! (4,501 reviews)
"While this hotel has a great location and offers a convenient commute to the parks, my experience was highly disappointing due to serious issues with management, security, and hidden costs. ​First, be aware of their parking policy. Parking is only complimentary if you book directly through the hotel. ..."

Reviewed on Jun 21, 2026

Kompose Boutique Resort at Theme Parks
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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.
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Frequently asked questions

How much does a Highland Meadows vacation package cost?
Get ready to book, because a getaway to Highland Meadows starts from a tempting CA $743. When you bundle your flights, hotels and car rentals into a package, you'll enjoy the best bargains.
How do I get a cheap travel package to Highland Meadows?
Find flights that fit your schedule, add a hotel to your booking and watch the savings stack up with a Highland Meadows vacation package. It's that simple! From flights and hotels to activities and rental cars, Expedia is your gateway to cheap travel. And with more than 550 airlines and 1,000,000 hotel options globally to pick from, you won't be short of choice.
Where should I stay in Highland Meadows?
A getaway to Highland Meadows isn't complete without stopping by Ridgewood Lakes Golf and Country Club, Lewis W Mathews Memorial Sports Complex and True Blue Winery. Stay close to these top attractions and make sightseeing simple.
What are the top hotels in Highland Meadows?
If it's comfort and convenience you'd like, you can't beat Beautiful And Spacious 5 Bed 4 Bath Home. Spend your nights relaxing here and your days discovering Highland Meadows's best attractions.
How far in advance should I book my Highland Meadows vacation?
It can be difficult to know when is the ideal time to book your vacation to Highland Meadows. But generally the earlier you book, the better the prices. Sometimes, you can lock in your flights and hotels up to 12 months before departure. If you're considering a last-minute getaway, no need to panic! There are plenty of fantastic bargains popping up on Expedia every single day.
What does an Expedia Highland Meadows travel package include?
It comes down to what you want. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Highland Meadows? A travel package including hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a Highland Meadows travel package?
Discover deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save a packet just by bundling your bookings. Whether you're embarking on a skiing adventure or sunning yourself on a warm beach, your dream getaway is only a few clicks away.
Can I choose my airline with a Highland Meadows Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Highland Meadows vacation package?
Because we know life can be unpredictable, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you've booked your Highland Meadows vacation package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Highland Meadows

ChampionsGate Golf Club

Enjoy a round of golf in Four Corners at ChampionsGate Golf Club. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

ChampionsGate Golf Club

Northeast Regional Park

Explore the lovely green spaces of Northeast Regional Park and enjoy the golf courses in Four Corners. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Northeast Regional Park

Highland Reserve Golf Club

Enjoy a round of golf in Davenport at Highland Reserve Golf Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Highland Reserve Golf Club

Things to do

"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

CA $118
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

CA $21
per adult
80% of travellers recommend
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Scenic One Hour Airboat Tour

Boggy Creek Scenic Everglades Airboat Tour

CA $61
per adult
98% of travellers recommend
Boggy Creek Scenic Everglades Airboat Tour
See all activities in Davenport
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.