Highland Meadows Vacations from $387

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Your Highland Meadows Vacation

Your next big adventure is just around the corner with a vacation package to Highland Meadows. Entertainment, relaxation and nothing but great times — you're sure to find it in this neighborhood. Your trip to Highland Meadows wouldn't be complete without stopping by leading attractions nearby such as Ridgewood Lakes Golf and Country Club, True Blue Winery and Lewis W Mathews Memorial Sports Complex. No matter your travel goals or budget, booking a perfect Highland Meadows vacation has never been easier with Expedia.

The Latest Highland Meadows Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,017, price is now $387 per person
$387
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,894, price is now $621 per person
$621
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.2/10 Exceptional! (1,002 reviews)
Clean room expected amenities

Reviewed on Nov 12, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $1,098, price is now $402 per person
$402
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (2,232 reviews)
We had a great time.

Reviewed on Nov 20, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,073, price is now $412 per person
$412
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful

Reviewed on Nov 22, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $1,399, price is now $594 per person
$594
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
19.2/10 Exceptional! (1,002 reviews)
Staff was super nice! Room was spacious and clean. The resturaunt cuisine was do tasty

Reviewed on Nov 23, 2025

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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

5/5(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
$82 nightly
The price is $92 total per night from Nov 30 to Dec 1
$92 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (3,942 reviews)
Great place to stay

Reviewed on Nov 18, 2025

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
$159 nightly
The price is $179 total per night from Nov 24 to Nov 25
$179 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (8,768 reviews)
Everything was great! The staff was amazing and service was awesome. The only reason I can’t give a full five is because the beds felt like laying on cardboard.

Reviewed on Nov 22, 2025

The Grove Resort & Water Park 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
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from Dec 14 to Dec 15
$108 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (2,634 reviews)
One of the best resorts I’ve stayed at. Everything was perfect.

Reviewed on Nov 21, 2025

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
See all 48,709 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

$15
per adult
80% of travellers recommend
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Orlando: Jet Ski Rentals from Lake Buena Vista Area

Orlando: Jet Ski Rentals from Lake Buena Vista Area

$79
per traveler
100% of travellers recommend
Orlando: Jet Ski Rentals from Lake Buena Vista Area
Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Polynesian Fire Luau with Dinner and Live Show

$75
per adult
84% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
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.