Anastasia Island Vacation Packages 2025/2026 from $325

Anastasia Island flight + hotel vacation packages

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

Florida Hotel & Conference Center in the Florida Mall

$325

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

Summerville Vacation Homes by Columbia Management

$592

per person

Jan 14 - Jan 21

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Orlando (MCO)

This vacation home features an outdoor pool and a gym. Bring the family and enjoy the free kid's club, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking and free WiFi.

Westgate Cocoa Beach Resort

$688

per person

Jan 4 - Jan 9

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 Vacation Villas Resort

Save 100% on your flight

$451

per person

Feb 15 - Feb 22

found 16 hours ago

Roundtrip 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.

Formosa Valley Resort by UNE Homes

$705

per person

Jan 14 - Jan 21

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool is featured at this vacation home, along with concierge services. Take advantage of the 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

$118 nightly

$132 total

Nov 30 - Dec 1

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.

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

300 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$191 total

Dec 7 - Dec 8

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.

Best Western Seaside Inn

541 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$144 total

Nov 30 - Dec 1

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.

Hilton Garden Inn St. Augustine Beach

401 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$115 total

Dec 4 - Dec 5

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.

Regency Inn & Suites

331 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$92 total

Dec 4 - Dec 5

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.

Holiday Inn Express St. Augustine Dtwn - Historic by IHG

601 Anastasia Blvd St. Augustine FL

Free Cancellation

$123 nightly

$137 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free on-the-go breakfast each morning.

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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

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

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

St. Augustine Lighthouse and Museum showing a lighthouse

St. Augustine Lighthouse & Maritime Museum

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 $325, 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.