Anastasia Island Vacation Packages 2026 from $265

Anastasia Island flight + hotel vacation packages

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

Westgate Town Center Resort

Save 100% on your flight

$265

per person

Apr 26 - Apr 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Westgate Vacation Villas Resort

$728

per person

Apr 30 - May 7

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

International Drive District

$284

per person

May 8 - May 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Westgate Cocoa Beach Resort

$890

per person

Apr 23 - Apr 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Westgate Towers Resort

Save 100% on your flight

$332

per person

Mar 25 - Mar 29

found 13 hours ago

Roundtrip flight included

New York (LGA) 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.

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

$143 nightly

$160 total

Feb 22 - Feb 23

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

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

300 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$213 nightly

$238 total

Feb 19 - Feb 20

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. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast.

Pool

Breakfast included

Best Western Seaside Inn

541 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$127 total

Feb 22 - Feb 23

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

$107 nightly

$119 total

Feb 22 - Feb 23

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

Regency Inn & Suites

331 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$76 total

Feb 23 - Feb 24

Total with taxes and fees

An indoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Parking included

Hilton Garden Inn St. Augustine Beach

401 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$118 total

Feb 22 - Feb 23

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.

Popular places to visit

St. Augustine Beach

4.5/5(1,934 reviews)

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

Anastasia State Park

4.5/5(473 reviews)

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

St. Augustine Lighthouse & Maritime Museum

4.5/5(859 reviews)

Enjoy spectacular views from the top of this lighthouse and learn about the history of the nation’s oldest port.

Frequently asked questions

How much are vacation packages to Anastasia Island?

Starting from as low as $265, 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.