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

Top Anastasia Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,191, price is now CA $760 per person
CA $760
per person
Sep 6 - Sep 13
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (3,629 reviews)
Excelente lugar,,todo bien limpio. Y personal muy amable.

Reviewed on Jun 21, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,463, price is now CA $875 per person
CA $875
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (6,626 reviews)
the staff is friendly and prompt when you need something and this is HUGE place. Big buth tub. Working microwave and fridge. I loved that there was a restaurant onsite, pizza place, a small store and two swimming pools. What i think they can do better is, there was no room service till we requested. Carpet needs upgrade.

Reviewed on Jun 21, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,829, price is now CA $1,723 per person
CA $1,723
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,009 reviews)
The cottage was wonderful. Stocked with everything you need just bring your food, drink and toilet paper! The cottage we stayed at was a perfect location just 5 minute walk to the amazing pool complex. The resort is great. Planning on going back soon.

Reviewed on Jun 20, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,630, price is now CA $1,015 per person
CA $1,015
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (507 reviews)
It was okay. They charged me with $250 as security deposit which I didn’t get back yet.

Reviewed on Jun 16, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,848, price is now CA $1,891 per person
CA $1,891
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (550 reviews)
Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien.

Reviewed on May 25, 2026

Where to stay in Anastasia Island

Find the best Anastasia Island areas and neighborhoods for the activities you enjoy most. Learn more about Anastasia Island
A sunset over the ocean with birds flying.

Butler Beach

5/5(1 area review)

Butler Beach is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to St. Augustine Beach or Butler Beach.

Find hotels in Butler Beach

Ready to book your vacation to Anastasia Island?

 

Choose your dates

Anastasia Island Hotel Deals

Guy Harvey Resort on St Augustine Beach

Guy Harvey Resort on St Augustine Beach

3 out of 5
860 A1A Beach Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jun 29 to Jun 30
CA $228
CA $254 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (3,106 reviews)
"Very nice hotel and the room was perfect"

Reviewed on Jun 22, 2026

Guy Harvey Resort on St Augustine Beach
Best Western Seaside Inn

Best Western Seaside Inn

2.5 out of 5
541 A1A Beach Boulevard St. Augustine FL
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jun 25 to Jun 26
CA $157
CA $175 total
Jun 25 - Jun 26
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"I had difficulty with several things while using this property. The room held two queen beds, with space for four people. However, the bathroom only had towels for three, and towel hanging hooks for two towels. There was plenty of free wall space to add towel bars for allow four people to dry their ..."

Reviewed on Jun 21, 2026

Best Western Seaside Inn
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

3.5 out of 5
300 A1A Beach Blvd St. Augustine FL
The price is CA $376 per night from Jul 8 to Jul 9
CA $376
CA $467 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (1,355 reviews)
"I loved everything about my stay. The room was clean, the food was delicious, and I enjoyed the amenities. I will definitely be going back."

Reviewed on Jun 19, 2026

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
See all 3,433 properties in Anastasia Island
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
Family Vacations
Family Vacations

Discover the most popular places to visit in Anastasia Island

St. Augustine Beach

St. Augustine Beach

4.5/5(51 reviews)

Nothing says vacation like spending a lazy day at St. Augustine Beach, a popular beach in St. Augustine. Experience the area's fascinating museums and great live music.

St. Augustine Beach
Anastasia State Park

Anastasia State Park

4.5/5(5 reviews)

Camp in the forest and relax on spectacular beaches when you visit one of Florida’s most beautiful state parks.

Anastasia State Park
St. Augustine Alligator Farm Zoological Park

St. Augustine Alligator Farm Zoological Park

4.5/5(3 reviews)

Feed and pet an alligator, hold a snake and meet a range of colorful and unusual reptiles and birds at one of Florida’s longest-running attractions.

St. Augustine Alligator Farm Zoological Park

What to do in Anastasia Island

Yoda and R2-D2 from Star Wars at Potter's Wax Museum in St. Augustine

Potter's Wax Museum

CA $29
per adult
96% of travellers recommend
Potter's Wax Museum
St. Augustine Live Music Sail with Drinks & Sunset Option

St. Augustine Live Music Sail with Drinks & Sunset Option

CA $108
per adult
80% of travellers recommend
St. Augustine Live Music Sail with Drinks & Sunset Option
Take a Scenic Boat Ride in St. Augustine

Take a Scenic Boat Ride in St. Augustine

CA $36
per adult
92% of travellers recommend
Take a Scenic Boat Ride in St. Augustine
See all activities in Anastasia Island

Frequently asked questions

Can I cancel my flight booking to Anastasia Island due to COVID-19?
In these difficult times, many carriers are offering more flexibility. Go to our Customer Service Portal to find important information about canceling or changing your Anastasia Island flight due to COVID-19.
What's the best way to find cheap flights to Anastasia Island that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to bring you the most flexible airfares on the market. Just click on "No change fee" directly below the "Flexible change policies" heading to find your dream flight to Anastasia Island.
What are some of the general tips for travelers to Anastasia Island during the COVID-19 outbreak?
The COVID-19 pandemic may have changed the way we travel, but it hasn't done away with our desire to explore. Here are a few tips on how to navigate travel's new challenges:
  • Before booking anything, check if any travel restrictions apply — in both your origin and destination. Get up-to-date information by reviewing government and airport websites.
  • Keep your face mask on during airport screening. A TSA officer will ask you to temporarily lower your mask for ID purposes.
  • You're no longer required to hand your boarding pass (electronic or paper) directly to a TSA officer. Rather, position your pass on the scanner and then hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on luggage. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag at the X-ray machine for scanning.
  • Put any personal items (e.g, keys, phone and wallet) in your carry-on rather than a bin to minimize handling during the screening process.
  • If you want to take food through security screening, put it in a clear plastic bag and then into a scanning bin. This lessens the likelihood that a TSA agent will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Anastasia Island?
Delta operates flights into or near Anastasia Island, including 1472 that travel to Orlando Intl. Airport (MCO) each month. Decide on your vacation dates and then book your fare early for the biggest bargain.
How can I find cheap tickets to Anastasia Island?
In the last seven days, was the lowest price for a flight to Anastasia Island. For an even better fare, book well in advance and be flexible with your travel dates. Search for your trip to Anastasia Island, then compare prices for nearby days by clicking on our "flexible dates" link.
How much is a flight to Anastasia Island?
If you were flying one way from (), you could've scored a bargain seat for in the last seven days. Round-trip flights to Anastasia Island ranged from only to during this same period.
What are the most popular airports to fly into in Anastasia Island?
The number one gateway to Anastasia Island, around 13460 flights land at Orlando Intl. Airport (MCO) every month. Find a top deal, book your fare and prepare to explore this amazing region.
When is the cheapest time to fly to Anastasia Island?
Fly out on a Tuesday to boost your chances of picking up the cheapest fare to Anastasia Island. Mondays are usually the next most affordable day to depart. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Anastasia Island?
In the last seven days, airfares varied between and . Take a look at our sensational deals to Anastasia Island, pick your favorite and get ready for your next fun vacation!
Which airlines with flights to Anastasia Island employ COVID-19 cleanliness policies?
Social distancing is only one small part of new aviation strategies to lessen the spread of COVID-19. From check-in to arrival, these carriers will bring you to Anastasia Island with comfort and confidence:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Spirit Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

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