Cheap Vacations in Anastasia Island

Choose two or more items and save on your trip:

3-night Anastasia Island vacations

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

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $410, price is now $221 per person
$221
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,149, price is now $533 per person
$533
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $490, price is now $301 per person
$301
per person
Apr 1 - Apr 4
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $641, price is now $402 per person
$402
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Harbor Island Beach Club by Villatel

Harbor Island Beach Club by Villatel

2 out of 5
Price was $2,195, price is now $1,405 per person
$1,405
per person
Apr 2 - Apr 5
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $503, price is now $326 per person
$326
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $533, price is now $345 per person
$345
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $474, price is now $309 per person
$309
per person
Apr 18 - Apr 21
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $670, price is now $450 per person
$450
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $702, price is now $473 per person
$473
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
Price was $910, price is now $629 per person
$629
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

4-night Anastasia Island vacations

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $404, price is now $258 per person
$258
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Resort on Cocoa Beach

The Resort on Cocoa Beach

3.5 out of 5
Save 100% on your flight
Price was $1,233, price is now $904 per person
$904
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
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 $561, price is now $329 per person
$329
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $543, price is now $325 per person
$325
per person
Mar 29 - Apr 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $775, price is now $481 per person
$481
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,114, price is now $714 per person
$714
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $553, price is now $361 per person
$361
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Fold Hotels Orlando

The Fold Hotels Orlando

2 out of 5
Save 100% on your flight
Price was $654, price is now $450 per person
$450
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $796, price is now $548 per person
$548
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Kenwood Inn

The Kenwood Inn

3.5 out of 5
Save 100% on your flight
Price was $1,181, price is now $816 per person
$816
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Save 100% on your flight
Price was $530, price is now $370 per person
$370
per person
Mar 29 - Apr 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,332, price is now $934 per person
$934
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

5-night Anastasia Island vacations

Price found within the past 48 hours. Click for updated prices.
Alhambra Villas

Alhambra Villas

3 out of 5
Save 100% on your flight
Price was $423, price is now $270 per person
$270
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $836, price is now $375 per person
$375
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,094, price is now $559 per person
$559
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $891, price is now $474 per person
$474
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
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 $715, price is now $391 per person
$391
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $534, price is now $296 per person
$296
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $654, price is now $378 per person
$378
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Save 100% on your flight
Price was $590, price is now $360 per person
$360
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $678, price is now $421 per person
$421
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Hard Rock Hotel Daytona Beach

Hard Rock Hotel Daytona Beach

4 out of 5
Save 100% on your flight
Price was $657, price is now $429 per person
$429
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Bahama House

Bahama House

3 out of 5
Save 100% on your flight
Price was $814, price is now $536 per person
$536
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)

6-7 night Anastasia Island vacations

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 $681, price is now $300 per person
$300
per person
Apr 14 - Apr 20
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
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 $1,000, price is now $505 per person
$505
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $687, price is now $357 per person
$357
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,302, price is now $689 per person
$689
per person
Mar 28 - Apr 4
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
Save 100% on your flight
Price was $759, price is now $417 per person
$417
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Save 100% on your flight
Price was $694, price is now $383 per person
$383
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
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 $862, price is now $476 per person
$476
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $926, price is now $519 per person
$519
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $966, price is now $555 per person
$555
per person
Apr 1 - Apr 8
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $677, price is now $394 per person
$394
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $578, price is now $351 per person
$351
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Flight deals to Anastasia Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Mar 3 - Wed, Mar 4
JFK
New York
MCO
Orlando
$56 Roundtrip, found 4 days ago
$56
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 3 from New York to Orlando, returning Wed, Mar 4, priced at $56 found 4 days ago
Mon, Mar 2 - Fri, Mar 6
LGA
New York
MCO
Orlando
$62 Roundtrip, found 4 days ago
$62
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Mon, Mar 2 from New York to Orlando, returning Fri, Mar 6, priced at $62 found 4 days ago
Mon, Feb 23 - Thu, Mar 5
PHL
Philadelphia
MCO
Orlando
$62 Roundtrip, found 6 days ago
$62
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Philadelphia to Orlando, returning Thu, Mar 5, priced at $62 found 6 days ago

Top rated hotels for your Anastasia Island vacation

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
1.34 mi from city center
$159 nightly
The price is $177 total per night
$177 total
Feb 26 - Feb 27
Total with taxes and fees
When you stay at Guy Harvey Resort on St Augustine Beach in St. Augustine, you'll be on the beach, within a 10-minute drive of Anastasia State Park and St. Augustine Beach.
Pool
Pet friendly
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
0.86 mi from city center
$193 nightly
The price is $215 total per night
$215 total
Mar 3 - Mar 4
Total with taxes and fees
With a stay at Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort in St. Augustine, you'll be on the beach, a 2-minute walk from St. Augustine Beach and a 4-minute drive from Anastasia State Park.
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
0.79 mi from city center
$116 nightly
The price is $129 total per night
$129 total
Feb 23 - Feb 24
Total with taxes and fees
When you stay at Courtyard by Marriott St. Augustine Beach in St. Augustine, you'll be by the ocean, a 1-minute drive from St. Augustine Beach and 5 minutes from Anastasia State Park.
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.