Anastasia Island Vacation Packages 2026 from $277

Anastasia Island flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$277

per person

Apr 26 - Apr 30

found 13 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.

Westgate Lakes Resort & Spa Universal Studios Area

$511

per person

Apr 22 - Apr 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and a free theme park shuttle.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$567

per person

Apr 29 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Cocoa Beach Resort

Save 100% on your flight

$685

per person

May 1 - May 4

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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$783

per person

Jun 4 - Jun 9

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.

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

$161 nightly

$180 total

Apr 13 - Apr 14

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

$135 nightly

$151 total

Apr 1 - Apr 2

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

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

300 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$222 nightly

$247 total

Mar 23 - Mar 24

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

Hampton Inn St. Augustine Beach

430 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$145 total

Mar 23 - Mar 24

Total with taxes and fees

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

Pool

Hot Tub

Americas Best Value Inn Ocean Inn

3955 A1A South Street St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$116 total

Apr 5 - Apr 6

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, luggage storage, and concierge services are also on offer.

Pool

Breakfast included

Courtyard by Marriott St. Augustine Beach

605 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$149 total

Apr 12 - Apr 13

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

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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 fascinating museums and great live music.

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 Alligator Farm Zoological Park

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.

Frequently asked questions

How much are vacation packages to Anastasia Island?

Starting from as low as $277, 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.