Deals on vacations and trips to Anastasia Island

Save when you book Anastasia Island package deals

Choose two or more items and save on your trip:

Anastasia Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $373, price is now $197 per person
$197
per person
Jan 29 - Feb 1
found 3 hours 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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $991, price is now $438 per person
$438
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free theme park shuttle. Business travelers can take advantage of the express check-out. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $747, price is now $364 per person
$364
per person
Jan 29 - Feb 1
found 1 day 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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $623, price is now $304 per person
$304
per person
Jan 21 - Jan 26
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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Save 100% on your flight
Price was $1,014, price is now $523 per person
$523
per person
Jan 29 - Feb 5
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

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
$118 nightly
The price is $132 total per night
$132 total
Nov 15 - Nov 16
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

Best Western Seaside Inn

2.5 out of 5
541 A1A Beach Boulevard St. Augustine FL
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $117 total per night
$117 total
Nov 29 - Nov 30
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
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
$204 nightly
The price is $227 total per night
$227 total
Dec 6 - Dec 7
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

Regency Inn & Suites

2 out of 5
331 A1a Beach Blvd St. Augustine FL
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $81 total per night
$81 total
Nov 16 - Nov 17
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
Ocean Breeze Inn

Ocean Breeze Inn

2 out of 5
311 A1A Beach Boulevard St. Augustine FL
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $65 total per night
$65 total
Nov 15 - Nov 16
Total with taxes and fees
This motel features 3 beach bars and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and a safe deposit box are also provided.
Pool
Parking included
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
$109 nightly
The price is $122 total per night
$122 total
Nov 15 - Nov 16
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
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.

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 $197, 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

A wooden bridge over water with a lighthouse in the background.
A brick building with a red roof, a lighthouse with alternating black and white stripes, and a clear blue sky with some clouds.
A lighthouse surrounded by dense forest and a marina with boats.
A lighthouse surrounded by lush greenery and a marina with boats.
A wooden boardwalk leading to a beach with dunes and sparse vegetation.

Explore More Ways to Travel with Travelocity