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 $619, price is now $352 per person
$352
per person
Nov 17 - Nov 22
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.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $2,474, price is now $1,332 per person
$1,332
per person
Oct 4 - Oct 11
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 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 $943, price is now $531 per person
$531
per person
Nov 16 - Nov 22
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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $872, price is now $505 per person
$505
per person
Nov 5 - Nov 9
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.
Tricove Inn & Suites

Tricove Inn & Suites

2.5 out of 5
Southside
Save 100% on your flight
Price was $594, price is now $359 per person
$359
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Jacksonville (JAX)
This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a computer station, and luggage storage are also offered.

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
Sep 7 - Sep 8
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
$98 nightly
The price is $109 total per night
$109 total
Sep 13 - Sep 14
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
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
$96 nightly
The price is $107 total per night
$107 total
Sep 10 - Sep 11
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.
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
$208 nightly
The price is $232 total per night
$232 total
Sep 30 - Oct 1
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.
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
$126 nightly
The price is $140 total per night
$140 total
Sep 9 - Sep 10
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.
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
$52 nightly
The price is $58 total per night
$58 total
Sep 7 - Sep 8
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.
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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 $352, 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 pier extending into calm water at sunset.
A wooden bridge over a river with alligators.
A historic building with a white porch and a large bell in the center.
A wooden boardwalk leading to a sign that reads "Land of Crocodiles."
A brick building with a red roof, a lighthouse with alternating black and white stripes, and a clear blue sky with some clouds.

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