A wooden pier extending into calm water at sunset.

Anastasia Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

The Latest Anastasia Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 9 - Jan 15

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.2/10 - Very good (2,136 reviews)
    "Good place"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,068
    CA $576
    per traveller
    found 1 day ago
    Westgate Vacation Villas Resort
  • Jan 9 - Jan 15

    Westgate Town Center Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.4/10 - Very good (2,082 reviews)
    "I always stay at this resort when I travel to Orlando with my family. I highly recommend!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,122
    CA $590
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Dec 18 - Dec 23

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    Save 100% on your flight
    CA $2,415
    CA $1,358
    per traveller
    found 20 hours ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Jan 24 - Jan 28

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (578 reviews)
    "The beaches across the street. The pools are nice however I had a room right next to the pool and they play music up until 9:00pm at night. So if you just trying to rest that will not happen. The music just kept playing all day long."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    Save 100% on your flight
    CA $1,703
    CA $966
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • Jan 15 - Jan 21

    Meliá Orlando Celebration + Flight

    Celebration
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,646 reviews)
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,659
    CA $974
    per traveller
    found 1 day ago
    Meliá Orlando Celebration

Discover the most popular places to visit in Anastasia Island

What to do in Anastasia Island

Anastasia Island Hotel Deals

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 an Anastasia Island vacation package cost?

Maybe less than you might think — from a low CA $576, actually! By combining flights, hotels and car rentals into a custom-built vacation package, your Anastasia Island escape is just clicks away.

How do I get a cheap travel package to Anastasia Island?

Book everything in the one place with our Anastasia Island vacation packages. You'll find deals on flights, hotels, tours and more that'll keep your wallet happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 properties around the world to pick from, there are endless opportunities to mix and match.

How far in advance should I book my Anastasia Island vacation?

Savvy travelers often book as early as possible. You can generally compare international fares on Expedia up to a year before your intended flight. If you're booking last minute, don't worry. Discounted prices sometimes become available in the last weeks before departure dates.

What does an Expedia Anastasia Island travel package include?

With Expedia, you can choose a combination of hotels, flights and car rentals to create your ideal Anastasia Island package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Don't forget, the more you bundle, the bigger the savings!

What should I know before booking an Anastasia Island travel package?

So many places to travel to, so many things to see. With a package, you'll be able to afford more of them. Bundle your flights, rental cars and hotels and make big savings.

Can I choose my airline with an Anastasia Island Expedia vacation package?

Yes — that's the beauty of an Expedia package. You get to choose. We have access to more than 550 partner airlines globally, so you have loads of choice when putting together your Anastasia Island escape.

If I'm not able to travel, can I cancel my Anastasia Island vacation package?

Yes, you can cancel your Anastasia Island booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.