Anastasia Island Vacation Packages 2025/2026 from $241

Anastasia Island flight + hotel vacation packages

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

Palazzo Lakeside Hotel

$241

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop 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

Save 100% on your flight

$729

per person

Nov 23 - Nov 29

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

$390

per person

Nov 13 - Nov 18

found 24 hours 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.

Bryan’s Spanish Cove

$488

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Palm Valley

Save 100% on your flight

$419

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, 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

$134 nightly

$150 total

Sep 16 - Sep 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

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

Sep 15 - Sep 16

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

Hampton Inn St. Augustine Beach

430 A1a Beach Blvd, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$141 total

Sep 17 - Sep 18

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

Best Western Seaside Inn

541 A1A Beach Boulevard, St. Augustine, FL

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Sep 16 - Sep 17

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

La Fiesta Ocean Inn And Suites

810 A1a Beach Blvd, St. Augustine, FL

$108 nightly

$121 total

Sep 16 - Sep 17

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

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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

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 great live music and fascinating museums.

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 $241, 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.