Deals on vacations and trips to Anastasia Island

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Anastasia Island flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
May 30 - Jun 4
Roundtrip 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

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
May 30 - Jun 4
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.
Alhambra Villas

Alhambra Villas

3 out of 5
Solivita
Save 100% on your flight
per person
Jun 17 - Jun 21
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and an outdoor tennis court. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. WiFi in public areas is free.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 4
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 4 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.
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
per person
Jun 6 - Jun 10
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 spa tub and perks like free self parking.

Top Anastasia Island hotel 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
The price is $143 per night
$143
per night
May 12 - May 13
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a terrace are also provided.
Pet friendly
Breakfast available
Castillo Real Resort Hotel

Castillo Real Resort Hotel

3 out of 5
530 A1a Beach Blvd, St. Augustine, FL
Free Cancellation
The price is $134 per night
$134
per night
May 20 - May 21
This hotel features an outdoor pool, a spa tub, and a restaurant. Enjoy the steam room and perks like free WiFi. Self parking, a grocery/convenience store, and express check-out are also offered.
Hot Tub
Breakfast available
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
The price is $196 per night
$196
per night
Apr 28 - Apr 29
This hotel 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.
Pet friendly
Breakfast included
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
The price is $65 per night
$65
per night
May 16 - May 17
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
The price is $68 per night
$68
per night
Apr 29 - Apr 30
The motel's outdoor pool, spa tub, and 3 beach bars are among the featured amenities. 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.
Hot Tub
Pool
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
The price is $76 per night
$76
per night
May 1 - May 2
This hotel doesn't skimp on freebies - guests receive free on-the-go 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.
Pet friendly
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

Image for St. Augustine 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 great live music and fascinating museums.

St. Augustine Beach
Image for St. George Street

St. George Street

4.5/5(1,670 reviews)

You can find the perfect gifts to bring home at St. George Street during your visit to St. Augustine. You can enjoy the coffeehouses while in the area.

St. George Street
Image for Flagler College

Flagler College

4.5/5(1,032 reviews)

Explore the campus of Flagler College, during your trip to St. Augustine. Discover the area's fascinating museums, or seek out its local tours.

Flagler College

Frequently asked questions

How much are vacation packages to Anastasia Island?
Adventure calls in Anastasia Island, with Travelocity vacation packages from as little as $263. Including both hotels and flights, these sensational deals make it super simple to explore every corner of the world.
Where can I get the best vacation package deals for Anastasia Island?
You can grab fantastic Anastasia Island package deals with Travelocity. Pick and choose from as many as 400 airlines and 1,000,000 properties worldwide and turn those vacation daydreams into a reality.
Why should I book my Anastasia Island vacation package via Travelocity?
By booking your hotel, flights, activities and car rental all in one place, you’ll save big bucks as well as precious time. We have a professional customer service support team available round-the-clock, and you’ll know that you’re always getting the best deal in town with our Price Match Guarantee. So, what’s stopping you? Book your dream getaway today and get packing!
Can I save money on my Anastasia Island car rental if I bundle it with hotels and flights?
Combining your bookings into an Anastasia Island vacation package will leave you with a nice chunk of spare change. You can choose a flight and car; a hotel, car and flight; or a hotel and car. You won’t find a better way to discover the greater Anastasia Island region than from behind the wheel of your own rental car. You can also add experiences and tours to your Travelocity package.
What is the best time of year to go to Anastasia Island?
If you’d rather avoid costly airfares, tourist hordes and a lack of vacancy, organize your getaway outside of January, February and March. The quietest time to travel to Anastasia Island is August, September and October. You’ll find the highest hotel rates in and the cheapest in .