Deals on vacations and trips to Anastasia Island

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Anastasia Island flight + hotel vacation packages

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

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $477, price is now $233 per person
$233
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,040, price is now $457 per person
$457
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop 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 Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $819, price is now $370 per person
$370
per person
Nov 1 - Nov 8
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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $826, price is now $383 per person
$383
per person
Nov 6 - Nov 11
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 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 Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $819, price is now $401 per person
$401
per person
Oct 27 - Nov 3
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.

Top Anastasia Island hotels deals

Guy Harvey Resort on St Augustine Beach

Guy Harvey Resort on St Augustine Beach

3 out of 5
860 A1A Beach Blvd, St. Augustine, FL
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $150 total per night
$150 total
Sep 1 - Sep 2
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

Courtyard by Marriott St. Augustine Beach

3 out of 5
605 A1A Beach Boulevard, St. Augustine, FL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $119 total per night
$119 total
Sep 1 - Sep 2
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
Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort

3.5 out of 5
300 A1A Beach Blvd, St. Augustine, FL
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $244 total per night
$244 total
Aug 27 - Aug 28
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
Quality Inn & Suites St Augustine Beach Area

Quality Inn & Suites St Augustine Beach Area

2.5 out of 5
901 A1A Beach Blvd, St. Augustine, FL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $80 total per night
$80 total
Aug 25 - Aug 26
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
Holiday Inn Express St. Augustine Dtwn - Historic by IHG

Holiday Inn Express St. Augustine Dtwn - Historic by IHG

2.5 out of 5
601 Anastasia Blvd, St. Augustine, FL
Free Cancellation
$113 nightly
The price is $126 total per night
$126 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an outdoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Hot Tub
La Fiesta Ocean Inn And Suites

La Fiesta Ocean Inn And Suites

2.5 out of 5
810 A1a Beach Blvd, St. Augustine, FL
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $131 total per night
$131 total
Aug 24 - Aug 25
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 showing landscape views, general coastal views and a beach

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.

St. Augustine Beach
Anastasia State Park

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.

Anastasia State Park
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.

St. Augustine Lighthouse & Maritime Museum

Frequently asked questions

How much are vacation packages to Anastasia Island?
Starting from as low as $233, 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.

Photos of local treasures

Browse Anastasia Island vacation photos for more inspiration

St. Augustine Lighthouse & Maritime Museum showing general coastal views and a sunset
St. Augustine Alligator Farm Zoological Park which includes zoo animals, dangerous animals and a bridge
St. Augustine Lighthouse and Museum featuring heritage elements
St. Augustine Alligator Farm Zoological Park showing signage and zoo animals as well as a small group of people
St. Augustine Lighthouse and Museum which includes a lighthouse