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 Towers Resort

Save 100% on your flight

$277

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Westgate Cocoa Beach Resort

Save 100% on your flight

$934

per person

Nov 24 - Nov 28

found 21 hours ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this traditional aparthotel. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$923

per person

Nov 29 - Dec 4

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.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$367

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip non-stop 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 mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

Disney's Animal Kingdom Lodge

Bay Lake

Save 100% on your flight

$1,039

per person

Nov 28 - Dec 1

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a theme park shuttle, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking.

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

$121 nightly

$135 total

Sep 22 - Sep 23

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

$105 nightly

$117 total

Sep 20 - Sep 21

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

Courtyard by Marriott St. Augustine Beach

605 A1A Beach Boulevard St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Sep 27 - Sep 28

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

$208 nightly

$232 total

Sep 28 - Sep 29

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

Regency Inn & Suites

331 A1a Beach Blvd St. Augustine FL

Free Cancellation

Reserve now, pay when you stay

$52 nightly

$58 total

Sep 14 - Sep 15

Total with taxes and fees

An indoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Parking included

9BR LUXURY OCEANFRONT ESTATE! LARGE HEATED POOL AND YARD AND SEPARATE GAME ROOM!

St. Augustine FL

Get rates

An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.

Pool

Kitchen

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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 $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.