Anastasia Island Vacation Packages 2026 from $267

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

$267

per person

Oct 21 - Oct 24

found 1 day 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.

Palazzo Lakeside Hotel

$295

per person

Oct 22 - Oct 26

found 1 day 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

$470

per person

Sep 6 - Sep 11

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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$444

per person

Sep 6 - Sep 11

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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$579

per person

Oct 15 - Oct 18

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

$129 nightly

$144 total

Aug 16 - Aug 17

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

Courtyard by Marriott St. Augustine Beach

605 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Aug 23 - Aug 24

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

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

300 A1A Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$216 nightly

$241 total

Aug 9 - Aug 10

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.

Best Western Seaside Inn

541 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$117 total

Aug 5 - Aug 6

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.

Quality Inn & Suites St Augustine Beach Area

901 A1A Beach Blvd St. Augustine FL

Free Cancellation

$64 nightly

$71 total

Aug 19 - Aug 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Hampton Inn St. Augustine Beach

430 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$141 total

Aug 5 - Aug 6

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

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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.

Stay near popular Anastasia Island attractions

A beach with waves, people, and buildings in the background.

St. Augustine Beach

9.2/10 (9,364 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.

See properties

Frequently asked questions

How much are vacation packages to Anastasia Island?

Starting from as low as $267, 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.