Anastasia Island Vacation Packages 2026 from $307

Anastasia Island flight + hotel vacation packages

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

Westgate Vacation Villas Resort

$307

per person

Sep 23 - Sep 30

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$496

per person

Sep 23 - Sep 30

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Westgate Towers Resort

Save 100% on your flight

$382

per person

Sep 15 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$935

per person

Sep 6 - Sep 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

WorldQuest Orlando Resort

Save 100% on your flight

$569

per person

Sep 15 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This aparthotel features an outdoor pool and a 24-hour gym. Families will appreciate the free theme park shuttle and onsite laundry facilities. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi.

Top Anastasia Island hotels deals

Guy Harvey Resort on St Augustine Beach

860 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$134 total

Aug 10 - Aug 11

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Pool

Pet friendly

Best Western Seaside Inn

541 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$146 total

Jul 19 - Jul 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free breakfast and free WiFi. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Pool

Breakfast included

Courtyard by Marriott St. Augustine Beach

605 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$114 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Pool

Free WiFi

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

300 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$210 nightly

$234 total

Aug 9 - Aug 10

Total with taxes and fees

This resort features 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the hot tub and free buffet breakfast.

Pool

Hot Tub

La Fiesta Ocean Inn And Suites

810 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$140 total

Aug 9 - Aug 10

Total with taxes and fees

An area shuttle is featured at this motel, along with an outdoor pool and a 24-hour front desk. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, express check-out, and a computer station are also on offer.

Pool

Breakfast included

Hilton Garden Inn St. Augustine Beach

401 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$127 total

Jul 23 - Jul 24

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Pool

Hot Tub

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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.

Stay near popular Anastasia Island attractions

A beach with waves, people, and buildings in the background.

St. Augustine Beach

9.2/10 (9,364 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.

See properties

Frequently asked questions

How much are vacation packages to Anastasia Island?

Starting from as low as $307, flight and hotel packages are the perfect way to stretch your vacation budget. Anastasia Island, here you come!

Where can I get the best vacation package deals for Anastasia Island?

There's no need to look any further than Travelocity. With 400 air carriers and 1,000,000 worldwide properties, it's easy to put together an Anastasia Island package deal that suits your travel style.

Why should I purchase my Anastasia Island vacation bundle with Travelocity?

From our 24/7 customer care to our range of enticing destinations, we're committed to fulfilling your travel dreams. All you need to do is to click and book — our Price Match Guarantee will ensure you lock in the best deal.

Can I save money on my Anastasia Island car rental if I combine it with hotels and flights?

Bundling your bookings into an Anastasia Island vacation package will leave you with some serious savings. Combine a car and flight; a hotel, car and flight; or a car and hotel. You won't find a better way to explore the greater Anastasia Island area than from the comfort of your own rental car. You can also add experiences and tours to your Travelocity package.