Cheap Vacations in Anastasia Island

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3-night Anastasia Island vacations

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

Seasons Florida Resort

2 out of 5
Price was $362, price is now $239 per person
$239
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip 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 $583, price is now $313 per person
$313
per person
Apr 7 - Apr 10
found 1 day ago
Roundtrip flight included
New York (NYC) 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 $1,021, price is now $600 per person
$600
per person
Apr 16 - Apr 19
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
Save 100% on your flight
Price was $675, price is now $404 per person
$404
per person
Apr 20 - Apr 23
found 1 day ago
Roundtrip non-stop 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 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 $552, price is now $342 per person
$342
per person
Apr 20 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,414, price is now $894 per person
$894
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 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 $474, price is now $309 per person
$309
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was $851, price is now $566 per person
$566
per person
Mar 28 - Mar 31
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Villas at Fortune Place

Villas at Fortune Place

3 out of 5
Save 100% on your flight
Price was $719, price is now $479 per person
$479
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 $938, price is now $636 per person
$636
per person
Mar 25 - Mar 28
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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $403, price is now $244 per person
$244
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $596, price is now $263 per person
$263
per person
Apr 9 - Apr 13
found 7 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $517, price is now $273 per person
$273
per person
Apr 15 - Apr 19
found 10 hours ago
Roundtrip non-stop 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 $592, price is now $340 per person
$340
per person
Mar 31 - Apr 4
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 $781, price is now $482 per person
$482
per person
Apr 17 - Apr 21
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 $932, price is now $593 per person
$593
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,120, price is now $715 per person
$715
per person
Apr 17 - Apr 21
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 $517, price is now $337 per person
$337
per person
Apr 19 - Apr 23
just found
Roundtrip flight included
New York (NYC) to Orlando (MCO)
The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5 out of 5
Price was $2,707, price is now $1,798 per person
$1,798
per person
Mar 28 - Apr 1
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,197, price is now $803 per person
$803
per person
Apr 12 - Apr 16
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 $884, price is now $596 per person
$596
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop 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 $396, price is now $248 per person
$248
per person
Apr 10 - Apr 15
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $842, price is now $393 per person
$393
per person
Mar 26 - Mar 31
found 7 hours ago
Roundtrip 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 $939, price is now $482 per person
$482
per person
Apr 6 - Apr 11
found 6 hours ago
Roundtrip flight included
New York (NYC) 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 $1,181, price is now $610 per person
$610
per person
Mar 26 - Mar 31
found 7 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
Save 100% on your flight
Price was $909, price is now $481 per person
$481
per person
Mar 26 - Mar 31
found 7 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 $661, price is now $369 per person
$369
per person
Mar 26 - Mar 31
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 $713, price is now $437 per person
$437
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

3.5 out of 5
Save 100% on your flight
Price was $461, price is now $297 per person
$297
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was $1,082, price is now $713 per person
$713
per person
Apr 1 - Apr 6
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 $985, price is now $654 per person
$654
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $531, price is now $358 per person
$358
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
found 1 day ago
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
Price was $1,143, price is now $469 per person
$469
per person
Apr 2 - Apr 9
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $1,078, price is now $448 per person
$448
per person
Apr 2 - Apr 9
found 23 hours 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 $1,631, price is now $803 per person
$803
per person
Apr 2 - Apr 9
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $1,301, price is now $646 per person
$646
per person
Mar 28 - Apr 4
found 1 hour ago
Roundtrip non-stop 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 $847, price is now $461 per person
$461
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 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 $563, price is now $336 per person
$336
per person
Mar 25 - Mar 31
found 1 day 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 $631, price is now $385 per person
$385
per person
Mar 30 - Apr 5
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
Save 100% on your flight
Price was $2,324, price is now $1,489 per person
$1,489
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
Save 100% on your flight
Price was $835, price is now $549 per person
$549
per person
Mar 30 - Apr 5
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 10 - Wed, Mar 11
JFK
New York
MCO
Orlando
$60 Roundtrip, found 1 day ago
$60
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 10 from New York to Orlando, returning Wed, Mar 11, priced at $60 found 1 day ago
Mon, Mar 2 - Fri, Mar 6
LGA
New York
MCO
Orlando
$62 Roundtrip, found 5 days ago
$62
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Mar 2 from New York to Orlando, returning Fri, Mar 6, priced at $62 found 5 days ago
Tue, Mar 3 - Tue, Mar 10
EWR
New York
MCO
Orlando
$64 Roundtrip, found 5 days ago
$64
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Mar 3 from New York to Orlando, returning Tue, Mar 10, priced at $64 found 5 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
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.
Pool
Breakfast included
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
0.74 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Feb 24 - Feb 25
Total with taxes and fees
With a stay at Best Western Seaside Inn in St. Augustine, you'll be near the beach, a 3-minute walk from St. Augustine Beach and a 5-minute drive from Anastasia State Park.
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.

^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.