Anastasia Island Vacation Packages

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Top Anastasia Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,324, price is now CA $742 per person
CA $742
per person
Jul 17 - Jul 24
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,007 reviews)
Everything was great

Reviewed on May 4, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,457, price is now CA $811 per person
CA $811
per person
Jul 17 - Jul 24
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,661 reviews)
That resort was amazing. The only thing missing was a breakfast restaurant because the Mexican restaurant that opened to serve breakfast wasn't very good and didn't offer many good options.

Reviewed on May 7, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,787, price is now CA $1,636 per person
CA $1,636
per person
Jul 18 - Jul 24
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Orlando (MCO)
9.2/10 Wonderful! (1,005 reviews)
Me and my fiancé got a cottage just for me and him and it was beautiful! It made us feel like we were at home with all the amenities we also cooked a home made meal they had all the pans, plates, etc.. we did have to rewash current stuff there was still food on them from who knows when. Also one of the pillow sheets were really dirty we just removed it. Other than that everything was amazing also we loved the H2O water park! We mostly differently will be back !

Reviewed on May 4, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $3,455, price is now CA $2,111 per person
CA $2,111
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (541 reviews)
Clean Room friendly staff

Reviewed on May 2, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,561, price is now CA $1,018 per person
CA $1,018
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
Our favorite place to stay at when we are in Orlando

Reviewed on Apr 28, 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
Birds flying over the ocean at sunrise

Butler Beach

1 out of top 10 points of interest in this area
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

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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 $195 per night from May 26 to May 27
CA $195
CA $218 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (3,021 reviews)
Great outdoor areas and the beach is a short walk

Reviewed on May 6, 2026

Guy Harvey Resort on St Augustine Beach
Hampton Inn St. Augustine Beach

Hampton Inn St. Augustine Beach

2.5 out of 5
430 A1a Beach Blvd St. Augustine FL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 26 to May 27
CA $167
CA $186 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
Terrific place to stay. Close proximity to good walkable dining, treats, and shops. Steps from the ocean with direct access to nice clean beach. Continental breakfast was very good with lots of choices, for kids and adults. Plenty of table space for brkfst dining. Fast check-in and check out with ...

Reviewed on May 6, 2026

Hampton Inn St. Augustine Beach
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
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Jun 2 to Jun 3
CA $288
CA $367 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (1,345 reviews)
Clean room and property!

Reviewed on May 5, 2026

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort
See all 3,405 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.
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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 $26
per adult
96% of travellers recommend
Potter's Wax Museum
Headstones in the ghosts and gravestones tour in St. Augustine

St. Augustine Haunted Tour : Ghosts & Gravestones

CA $53
per adult
84% of travellers recommend
St. Augustine Haunted Tour : Ghosts & Gravestones
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.

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