Anastasia Island Vacation Packages 2025/2026 from $262

Anastasia Island flight + hotel vacation packages

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

Palazzo Lakeside Hotel

Save 100% on your flight

$262

per person

Nov 6 - Nov 13

found 2 days ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$345

per person

Nov 1 - Nov 5

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 Lakes Resort & Spa Universal Studios Area

$462

per person

Nov 6 - Nov 13

found 2 days 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 Cocoa Beach Resort

$722

per person

Nov 16 - Nov 21

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Boardwalk Inn and Suites

Davis

Save 100% on your flight

$380

per person

Dec 18 - Dec 24

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free valet parking and free WiFi. There's a hot tub on site, and a 24-hour front desk and a communal living room are also provided.

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

$134 nightly

$150 total

Oct 5 - Oct 6

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

$209 nightly

$233 total

Oct 21 - Oct 22

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

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

Oct 5 - Oct 6

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 perks like free self parking.

Pool

Parking included

Quality Inn & Suites St Augustine Beach Area

901 A1A Beach Blvd, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$89 total

Oct 2 - Oct 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

La Fiesta Ocean Inn And Suites

810 A1a Beach Blvd, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$134 total

Oct 6 - Oct 7

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

$110 nightly

$122 total

Oct 5 - Oct 6

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

Don't see what you're looking for?

See all available properties in Anastasia Island

View all properties

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 $262, 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.