Anastasia Island Vacation Packages 2025/2026 from $298

Anastasia Island flight + hotel vacation packages

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

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

per person

Sep 21 - Sep 25

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.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Vilano Beach

Save 100% on your flight

per person

Oct 9 - Oct 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

The private beach and full-service spa are among the highlights at this hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

per person

Sep 21 - Sep 25

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 Vacation Villas Resort

Save 100% on your flight

per person

Sep 29 - Oct 5

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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

per person

Oct 1 - Oct 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

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

$152 nightly

$170 total

Aug 10 - Aug 11

Total includes 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

$200 nightly

$223 total

Aug 19 - Aug 20

Total includes 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

Quality Inn & Suites St Augustine Beach Area

901 A1A Beach Blvd, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$86 total

Aug 4 - Aug 5

Total includes 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

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

Aug 10 - Aug 11

Total includes 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

Americas Best Value Inn Ocean Inn

3955 A1A South Street, St. Augustine Beach, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$82 total

Aug 4 - Aug 5

Total includes 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

Castillo Real Resort Hotel

530 A1a Beach Blvd, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$156 total

Jul 24 - Jul 25

Total includes taxes and fees

This hotel features an outdoor pool and a hot tub. WiFi in public areas is free. Valet parking is offered and multilingual staff can provide around-the-clock assistance.

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

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 fascinating museums and great live music.

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 and Museum showing a lighthouse

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 $298, 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.