Cheap Flights to Anastasia Island from $34

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How Much Does it Cost To Fly To Anastasia Island?

The cheapest prices found with in the last 7 days for return flights were $87 and $34 for one-way flights to Anastasia Island for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Nov 14 - Wed, Nov 18
IAD
Washington Dulles Intl.
MCO
Orlando Intl.
$87 Roundtrip, found 7 hours ago
$87
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Washington Dulles Intl. to Orlando Intl., returning Wed, Nov 18, priced at $87 found 7 hours ago
Wed, Dec 2 - Sat, Dec 5
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$115 Roundtrip, found 22 hours ago
$115
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Sat, Dec 5, priced at $115 found 22 hours ago
OriginDestinationTravel DatesFlights From*
PHLJacksonvilleDecember 5 to December 12$88
PSMOrlandoOctober 31 to November 7$113
EWRJacksonvilleDecember 2 to December 5$115
EWRJacksonvilleDecember 2 to December 5$115
SWFOrlandoOctober 24 to October 30$145
AUSOrlandoDecember 7 to December 10$147
EWROrlandoDecember 7 to December 12$178
DCAJacksonvilleDecember 7 to December 12$269
LGADaytona BeachOctober 22 to October 26$271
JFKJacksonvilleDecember 2 to December 5$279
BOSJacksonvilleDecember 2 to December 5$279
BOSDaytona BeachNovember 4 to November 14$315
JFKDaytona BeachOctober 17 to October 24$323
AUSDaytona BeachNovember 14 to November 22$357
PHLDaytona BeachNovember 11 to November 24$372
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SWFOrlandoOctober 10 to October 22$202
PHLJacksonvilleOctober 10 to October 12$250
ORDOrlandoOctober 10 to October 11$297
EWROrlandoOctober 11 to October 25$321
JFKJacksonvilleOctober 10 to October 14$424
LGAJacksonvilleOctober 10 to October 14$424
BWIJacksonvilleOctober 11 to October 17$431
EWRJacksonvilleOctober 10 to October 11$453
JFKOrlandoOctober 11 to October 17$458
JFKDaytona BeachOctober 10 to October 13$468
BOSDaytona BeachOctober 10 to October 14$564
PHLDaytona BeachOctober 11 to October 18$586
BOSJacksonvilleOctober 10 to October 11$587
AUSDaytona BeachOctober 9 to October 12$587
AUSJacksonvilleOctober 10 to October 13$588
*Prices include taxes and fees

Anastasia Island Flight Information

Traveling to
Anastasia Island
Lowest Price
$87
Number of Airlines Serving
Airlines Serving
Frontier Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Anastasia Island Accommodation Deals

Ocean Breeze Inn

Ocean Breeze Inn

2 out of 5
311 A1A Beach Boulevard St. Augustine FL
$55 nightly
The price is $62 total per night from Oct 4 to Oct 5
$62 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and 3 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,155 reviews)
"Room was clean, AC worked. Only downside was the bedding was damp both days. Maybe the dryer wasn't working."

Reviewed on Oct 1, 2026

Opens in a new windowOcean Breeze Inn
Regency Inn & Suites

Regency Inn & Suites

2 out of 5
331 A1a Beach Blvd St. Augustine FL
$76 nightly
The price is $84 total per night from Oct 4 to Oct 5
$84 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,287 reviews)
"Hotel was clean, area was nice and staff was very helpful. Walking distance to beach, restaurants and stores. Very safe area."

Reviewed on Oct 1, 2026

Opens in a new windowRegency Inn & Suites
Americas Best Value Inn Ocean Inn

Americas Best Value Inn Ocean Inn

2 out of 5
3955 A1A South Street St. Augustine FL
$76 nightly
The price is $84 total per night from Oct 4 to Oct 5
$84 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowAmericas Best Value Inn Ocean Inn
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The Anastasia Inn

The Anastasia Inn

2.5 out of 5
218 Anastasia Boulevard St. Augustine FL
$64 nightly
The price is $71 total per night from Oct 4 to Oct 5
$71 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,001 reviews)
"Good bargain for a clean & comfortable place."

Reviewed on Sep 23, 2026

Opens in a new windowThe Anastasia Inn
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.

Luxury Hotels in Anastasia Island

Ocean Breeze Inn

Ocean Breeze Inn

2 out of 5
311 A1A Beach Boulevard St. Augustine FL
$55 nightly
The price is $62 total per night from Oct 4 to Oct 5
$62 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and 3 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,155 reviews)
"Room was clean, AC worked. Only downside was the bedding was damp both days. Maybe the dryer wasn't working."

Reviewed on Oct 1, 2026

Opens in a new windowOcean Breeze Inn
Quality Inn & Suites St Augustine Beach Area

Quality Inn & Suites St Augustine Beach Area

2.5 out of 5
901 A1A Beach Blvd St. Augustine FL
$63 nightly
The price is $70 total per night from Oct 22 to Oct 23
$70 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and ...
7.2/10 Good! (1,002 reviews)
"This property is not well maintained. Considering that this is budget type Inn, this should be expected. One thing I like is the location. It's within walking distance to the beach which is really nice for a dip in the Atlantic Ocean."

Reviewed on Oct 1, 2026

Opens in a new windowQuality Inn & Suites St Augustine Beach Area
Castillo Real St. Augustine Beach,Tapestry Collection Hilton

Castillo Real St. Augustine Beach,Tapestry Collection Hilton

3 out of 5
530 A1a Beach Blvd St. Augustine FL
$127 nightly
The price is $141 total per night from Oct 12 to Oct 13
$141 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the ...
8.6/10 Excellent! (145 reviews)
"been there 17 times - can walk to the beach and breakfast is the best!"

Reviewed on Sep 24, 2026

Opens in a new windowCastillo Real St. Augustine Beach,Tapestry Collection Hilton
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Americas Best Value Inn Ocean Inn

Americas Best Value Inn Ocean Inn

2 out of 5
3955 A1A South Street St. Augustine FL
$76 nightly
The price is $84 total per night from Oct 4 to Oct 5
$84 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowAmericas Best Value Inn Ocean Inn
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.

Family Friendly Hotels in Anastasia Island

Courtyard by Marriott St. Augustine Beach

Courtyard by Marriott St. Augustine Beach

3 out of 5
605 A1A Beach Boulevard St. Augustine FL
$98 nightly
The price is $109 total per night from Oct 18 to Oct 19
$109 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
Opens in a new windowCourtyard by Marriott St. Augustine Beach
Castillo Real St. Augustine Beach,Tapestry Collection Hilton

Castillo Real St. Augustine Beach,Tapestry Collection Hilton

3 out of 5
530 A1a Beach Blvd St. Augustine FL
$127 nightly
The price is $141 total per night from Oct 12 to Oct 13
$141 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Augustine. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the ...
8.6/10 Excellent! (145 reviews)
"been there 17 times - can walk to the beach and breakfast is the best!"

Reviewed on Sep 24, 2026

Opens in a new windowCastillo Real St. Augustine Beach,Tapestry Collection Hilton
Ocean Breeze Inn

Ocean Breeze Inn

2 out of 5
311 A1A Beach Boulevard St. Augustine FL
$55 nightly
The price is $62 total per night from Oct 4 to Oct 5
$62 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free WiFi, free parking, and 3 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,155 reviews)
"Room was clean, AC worked. Only downside was the bedding was damp both days. Maybe the dryer wasn't working."

Reviewed on Oct 1, 2026

Opens in a new windowOcean Breeze Inn
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La Fiesta Ocean Inn And Suites

La Fiesta Ocean Inn And Suites

2.5 out of 5
810 A1a Beach Blvd St. Augustine FL
$129 nightly
The price is $144 total per night from Oct 4 to Oct 5
$144 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this motel in St. Augustine. Enjoy free breakfast, free WiFi, and an area shuttle (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
"The bathroom was probably the worst part of the room. It had mold in the shower curtain in the shower was soft on the floor. It seem like there was water getting underneath the tub. The room itself was fine. The pool was good and the beach access was pretty good."

Reviewed on Oct 1, 2026

Opens in a new windowLa Fiesta Ocean Inn And Suites
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.

Best Anastasia Island Flight and Hotel Packages

Anastasia Island flight + hotel packages - economy flights

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

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $856, price is now $460 per person
$460
per person
Nov 3 - Nov 10
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Price was $2,851, price is now $1,531 per person
$1,531
per person
Nov 25 - Nov 30
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $1,019, price is now $562 per person
$562
per person
Nov 1 - Nov 9
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Don't see what you're looking for?
See all available trips from Boston to Anastasia Island
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Anastasia Island flight + hotel packages - first class flights

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

Seasons Florida Resort

2 out of 5
Price was $1,298, price is now $1,033 per person
$1,033
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $2,236, price is now $1,557 per person
$1,557
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $1,974, price is now $1,521 per person
$1,521
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Don't see what you're looking for?
See all available trips from Chicago to Anastasia Island
View all trips

Need a Car For After Your Flight?

Midsize

  • 5 people
  • Unlimited mileage
Orlando, USA

$4

$8 total
found 6 hours ago
Midsize undefined

Compact

  • 5 people
  • Unlimited mileage
Orlando, USA

$4

$8 total
found 6 hours ago
Compact undefined

Economy

  • 5 people
  • Unlimited mileage
Orlando, USA

$4

$8 total
found 6 hours ago
Economy undefined

Standard

  • 5 people
  • Unlimited mileage
Orlando, USA

$5

$10 total
found 6 hours ago
Standard undefined
Lowest prices found within the past 6 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I fly to Anastasia Island right now?
Before you lock your flights in, take a look through Travelocity's Covid-19 Travel Advisor. Enter your origin, destination, travel dates and vaccination status to check if any additional rules or restrictions apply, such as the need to quarantine. It's important to corroborate the advice with official government websites as well as your travel insurance company.
How much is the cheapest flight to Anastasia Island?
Your next vacation doesn't have to make a huge dent in your budget. Within the last seven days, the cheapest roundtrip flight to Anastasia Island cost $87. Find a bargain fare and spend the dollars you save on awesome experiences. This price was available on Travelocity for flights to Anastasia Island departing within the next year. Prices and availability are subject to change. Additional terms apply.
If I cannot travel due to COVID-19, can I change my booking to a later date?
Our useful Customer Service Portal link has all the info you'll need about making changes or cancellations to your flight. Before you lock in your tickets to Anastasia Island, be sure to check the terms and conditions of your chosen airline too.
What is the cheapest month to fly to Anastasia Island?
According to Travelocity's direct return flight demand from January to December last year, November is the cheapest time to jump on a plane to Anastasia Island. Keep an eye out for flights during this month and snare a terrific bargain today.
How can I check my flight status to Anastasia Island?
Take advantage of Travelocity's customer portal, Trips. You'll find almost everything related to your flight to Anastasia Island here, including valuable information about gate numbers, flight status and more. You'll see Trips at the top right of the Travelocity homepage. Simply sign up, log in and find what you need. You can also access your itinerary on the move and get real-time travel updates with the Travelocity app. You'll find all your itineraries in one convenient place, making it a snap to share details with any members of your family flying with you.
How do I find the best deals on flights to Anastasia Island?
One of the easiest ways to find an epic deal is to be flexible with your dates. Begin by searching for your flight to Anastasia Island, then tap on the "Flexible dates" box at the top of the results. This will show you prices for nearby dates. Like another tip? Book sooner than later. To give you an idea of fares, $87 was the cheapest price for a return flight to Anastasia Island in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Anastasia Island with Travelocity?
Where to begin! With our cheap flights to Anastasia Island, rental cars and activities, you'll discover all you need for an awesome getaway with Travelocity. Reserve your cheap family flights and take advantage of our round-the-clock customer assistance and Price Match Guarantee if necessary. Our aim is to provide hassle-free travel every time you book with us so that you can spend less time worrying and more time having fun with your travel buddies.
What are the most popular flight routes to Anastasia Island?
To help you find great flights to Anastasia Island, here's a list of some of the most popular routes:

  • Newark, NJ (EWR-Liberty Intl.) to Orlando Intl. Airport (MCO) - 3,839 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Orlando Intl. Airport (MCO) - 3,536 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Orlando Intl. Airport (MCO) - 2,769 flights a month.

How much is a flight to Anastasia Island on average?
Travelers have found roundtrip flights to Anastasia Island for between $87 and $588 with Travelocity in the last seven days. Whether you're planning to fly economy or first class, we'll help you get a fantastic deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Anastasia Island?
Below you'll find a selection of top direct flights to Anastasia Island and their average journey times:

  • Newark, NJ (EWR-Liberty Intl.) to Orlando Intl. Airport (MCO) - 2 hours and 54 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Orlando Intl. Airport (MCO) - 1 hour and 37 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Orlando Intl. Airport (MCO) - 2 hours and 34 minutes

What can I expect on a flight to Anastasia Island?
Factors such as your airline and your place of departure will mostly determine what's offered on your trip. You'll likely find all sorts of flights to Anastasia Island, from cheap flights for family vacations to business class journeys. Hot meals, drinks and entertainment are a taste of what most airlines offer on long-haul flights.

Plane Tickets To Anastasia Island

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Anastasia Island. Browse through our inventory to explore a wide range of cheap flights to Anastasia Island to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Anastasia Island as you anxiously await to exit the plane and explore what Anastasia Island has to offer. Considering all the amazing local food and culture in Anastasia Island, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Anastasia Island to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Anastasia Island without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Anastasia Island with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Anastasia Island today!

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.