Highland Meadows Holidays

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Our guide on 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

Though Watersong may not have many top sights, you can venture to the surrounding area to see attractions like Providence Golf Club and Reunion Resort Golf Course.

Find hotels in Watersong

Our pick of the best Highland Meadows Hotel Deals

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 NZ$416 per night from 12 Jan to 13 Jan
NZ$416
12 Jan - 13 Jan
includes taxes & fees
8/10 Very Good! (8,956 reviews)
Our overall experience was phenomenal. Our children aren’t interested in theme parks and we aren’t interested in dining out 3 times a day so The Grove checks all the boxes. I would recommend to management to invest in common area upkeep.

Reviewed on 6 Jan 2026

The Grove Resort & Water Park Orlando
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 NZ$216 per night from 28 Jan to 29 Jan
NZ$216
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (4,245 reviews)
Was there over Christmas break, which is the busiest time of year in Orlando, but the property is spread out enough that it didn’t feel overcrowded.

Reviewed on 4 Jan 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr Orlando FL
The price is NZ$232 per night from 1 Feb to 2 Feb
NZ$232
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (2,845 reviews)
Spacious room and beautiful property

Reviewed on 4 Jan 2026

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
See all 48,601 properties in Highland Meadows
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.

Frequently asked questions

How much does a Highland Meadows holiday package cost?
Get ready to book, because a getaway to Highland Meadows starts from a tempting . 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 holiday 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 holiday?
It can be difficult to know when is the ideal time to book your holiday 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 travelling 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 holiday 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 holiday 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 holiday 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

Lewis W Mathews Memorial Sports Complex

Explore the lovely green spaces of Lewis W Mathews Memorial Sports Complex and enjoy the golf courses in Davenport. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

Lewis W Mathews Memorial Sports Complex

Activities

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

NZ$26
per adult
80% of travellers recommend
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Polynesian Fire Luau with Dinner and Live Show

NZ$128
per adult
80% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

NZ$95
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
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.