Lakeside Estates Vacations from $288

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 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

Your Lakeside Estates Vacation

Organizing your next travel adventure just got simpler with a vacation package to Lakeside Estates. Experience everything this neighborhood has to offer while creating fond memories you won't forget. When it's time to head out and explore, you'll find loads of big-name attractions nearby including Osceola Heritage Park, Kissimmee Lakefront Park and Silver Spurs Arena. Visit one, two (or even all!) during your trip to Lakeside Estates. No matter what your ideal Lakeside Estates vacation may look like, you can turn it into reality with Expedia.

The Latest Lakeside Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Orbit One Vacation Villas

Orbit One Vacation Villas

3 out of 5
Save 100% on your flight
Price was $557, price is now $288 per person
$288
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.4/10 Exceptional! (1,408 reviews)
I absolutely love staying here. This is our home away from home. We stayed in an updated unit. It was so beautiful. Everything is perfect. If you need an additional supplies they provide it to you. Laundry soap, dish soap, body wash, shampoo, conditioner, and extra blankets! They even let us borrow fans to sleep. This place is the place to stay. Thank you to the staff for being on top on everything. :).

Reviewed on Oct 14, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,336, price is now $656 per person
$656
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
Excellent property to go too. Lazy river was night and the staff at the front desk was amazing. Very close to the beach with many restaurants and shops to walk too. Even saw Space X launch a rocket from this location. Perfect spot for a great price. Recommend especially if you're bring Children.

Reviewed on Oct 10, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $799, price is now $400 per person
$400
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Great place for families!!!

Reviewed on Oct 14, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,475, price is now $738 per person
$738
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
Love this place, but the cleaning staff can do a better job with the rooms.

Reviewed on Oct 13, 2025

Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $1,004, price is now $504 per person
$504
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.4/10 Exceptional! (1,002 reviews)
Very clean well maintained quiet property in a great location. Very nice pool and hot tub on the lake. They have fishing tackle that we used. Also kayaks, paddle boats and pool toys. Was nice and quiet compared to the large larger resorts that charge for these activities but also have a ton of people. Highly recommend this place.

Reviewed on Oct 1, 2025

Where to stay in Lakeside Estates

Find the best Lakeside Estates areas and neighborhoods for the activities you enjoy most. Learn more about Lakeside Estates
International Drive showing landscape views

International Drive District

1 out of top 10 points of interest in this area

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Lakeside Estates Hotel Deals

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $123 total per night from Oct 29 to Oct 30
$123 total
Oct 29 - Oct 30
Total with taxes and fees
7.4/10 Good! (6,189 reviews)
"There was clothes from previous tenants left under bathroom sink which makes me question the cleanliness."

Reviewed on Oct 12, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Nov 5 to Nov 6
$150 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (5,395 reviews)
"Loved it."

Reviewed on Oct 13, 2025

Universal's Cabana Bay Beach Resort
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
$91 nightly
The price is $103 total per night from Nov 4 to Nov 5
$103 total
Nov 4 - Nov 5
Total with taxes and fees
9.2/10 Wonderful! (3,678 reviews)
"This place is awesome! Rooms are huge for the price."

Reviewed on Oct 12, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 50,824 properties in Lakeside Estates
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 Lakeside Estates

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

4.5/5(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

4.5/5(4,155 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$42
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$192
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.