Country Crossing Holidays

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Your Country Crossing Holiday

Make planning your travels easy by snapping up a holiday package to Country Crossing. We'll look after all the details, so you can concentrate on appreciating everything this neighbourhood can offer. Your trip to Country Crossing wouldn't be complete without a stop at leading attractions nearby such as Osceola Heritage Park, Silver Spurs Arena and The Ice Factory of Central Florida. Stop daydreaming and start doing. When it's time to lock in your dream holiday to Country Crossing, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
  • Lounge
    Jul 7 - Jul 13

    Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes + Flight

    Kissimmee
    6 nights
    4.0 star property
    10/10 - Exceptional (4 reviews)
    "Clean, close to disney, easy accessibility and arround alot of good restaurants and shops"
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Orlando (MCO)
    SYD - MCO • 2 stops MCO - SYD • 2 stops
    AU$3,271
    AU$2,828
    per traveller
    found 1 day ago
    Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
  • Aerial view
    Jul 7 - Jul 13

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    "THE HOSPITALITY OF THE PEOPLE AND THE CLEANLINESS OF THE PROPERTY WERE BEAUTIFUL 😍 WE'RE PLANNING TO STAY THERE AGAIN IN AUGUST 2026 FOR A WEEK THIS TIME. WE LOVED EVERY SECOND ❤️ JULIANNE COVINGTON"
    Reviewed June 1, 2026
    Return • Sydney (SYD) - Orlando (MCO)
    SYD - MCO • 2 stops MCO - SYD • 2 stops
    AU$4,780
    AU$3,320
    per traveller
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Waterslide
    Jul 7 - Jul 13

    Evermore Orlando Resort + Flight

    Orlando
    6 nights
    4.0 star property
    9.6/10 - Exceptional (684 reviews)
    "Beautiful site and homes. Amazing pool and amenities"
    Reviewed May 31, 2026
    Return • Sydney (SYD) - Orlando (MCO)
    SYD - MCO • 2 stops MCO - SYD • 2 stops
    AU$6,509
    AU$5,147
    per traveller
    found 1 day ago
    Evermore Orlando Resort
  • Outdoor pool, pool umbrellas, pool loungers
    Jul 7 - Jul 13

    Magic Village Yards, Trademark Collection by Wyndham + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,189 reviews)
    "Great place to stay."
    Reviewed May 5, 2026
    Return • Sydney (SYD) - Orlando (MCO)
    SYD - MCO • 2 stops MCO - SYD • 2 stops
    AU$3,592
    AU$3,038
    per traveller
    found 1 day ago
    Magic Village Yards, Trademark Collection by Wyndham
  • Outdoor pool, open 9:00 AM to 6:00 PM, free pool cabanas, pool umbrellas
    Jul 7 - Jul 13

    ette hotel + Flight

    Kissimmee
    6 nights
    5.0 star property
    9.6/10 - Exceptional (452 reviews)
    "."
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Orlando (MCO)
    SYD - MCO • 2 stops MCO - SYD • 2 stops
    AU$3,796
    AU$3,292
    per traveller
    found 1 day ago
    ette hotel

Our guide on where to stay in Country Crossing

Find the best Country Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Country Crossing
International Drive District

International Drive District

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

Our pick of the best Country Crossing 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 AU$233 per night from 4 June to 5 June
AU$233
4 June - 5 June
includes taxes & fees
9.2/10 Wonderful! (5,649 reviews)
"Great location on the beach."

Reviewed on 1 June 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 15 June to 16 June
AU$153
15 June - 16 June
includes taxes & fees
8.6/10 Excellent! (6,943 reviews)
"Great visit"

Reviewed on 1 June 2026

DoubleTree by Hilton at the Entrance to Universal 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 AU$341 per night from 7 June to 8 June
AU$341
7 June - 8 June
includes taxes & fees
8/10 Very Good! (10,044 reviews)
"Change my room the next day. Down grade my room And still charge the same . Ask for things the come with the room never never received them. Too much walking."

Reviewed on 1 June 2026

The Grove Resort & Water Park Orlando
See all 46,168 properties in Country Crossing
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Country Crossing holiday package cost?
From as low as , you can handcraft your own Country Crossing package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Country Crossing?
Search for flights that fit in with your schedule, add a hotel to your booking and watch the savings pile up with a Country Crossing holiday package. It's that easy! From flights and hotels to rental cars and activities, Expedia makes travelling on the cheap easy. And with more than 550 air carriers and 1 000 000 hotel options around the world to choose from, you won't be short of choice.
Where should I stay in Country Crossing?
Stay within walking distance of ChampionsGate Golf Club. This top attraction is in the thick of the action and on the must-see lists of many urban explorers.
How far in advance should I book my Country Crossing holiday?
While not all airlines release tickets early, you can normally compare international fares on Expedia up to a year in advance. This is the time you'll bag some fantastic bargains. If you're booking at the last minute, you might get lucky. Discounted prices occasionally appear just weeks before departure.
What does an Expedia Country Crossing travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Country Crossing package that suits you. Heading away for a few weeks? Look into a flight, rental car and hotel bundle. If you can only manage a quick getaway, a hotel and airfare deal could be more your style. Activities can also be added after you've booked. Our travel packages make it easy to save and plan.
What should I know before booking a Country Crossing travel package?
When you book your flights, hotels and car rentals together, you'll pick up awesome discounts. Whether you're planning a rural escape in a cottage or want to stay in an upscale city hotel, Expedia can help make it happen.
Can I choose my airline with a Country Crossing Expedia holiday package?
Yes — and it's easy 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 Country Crossing holiday package?
If your travel plans in Country Crossing have changed, it's comforting to know that it's possible to cancel your booking. If your booking was made within the last 24 hours, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Country Crossing

Universal Orlando Resort

Universal Orlando Resort

4.5/5(30 reviews)

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

Universal Orlando Resort
Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(9 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(49 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

Universal Studios Florida

Activities

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

AU$53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$260
per adult
Walt Disney World® Resort Theme Park 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

AU$38
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
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.