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.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $409, price is now $231 per person
$231
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
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 $1,043, price is now $631 per person
$631
per person
Oct 2 - Oct 5
found 2 days 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 $660, price is now $418 per person
$418
per person
Oct 2 - Oct 5
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $591, price is now $392 per person
$392
per person
Oct 22 - Oct 25
found 1 hour 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 $708, price is now $472 per person
$472
per person
Oct 2 - Oct 5
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Siena at Bella Collina

Siena at Bella Collina

3.5 out of 5
Save 100% on your flight
Price was $1,223, price is now $849 per person
$849
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Amelia by the Sea

Amelia by the Sea

4 out of 5
Save 100% on your flight
Price was $4,401, price is now $3,089 per person
$3,089
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Jacksonville (JAX)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $530, price is now $375 per person
$375
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Price was $877, price is now $624 per person
$624
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Price was $540, price is now $389 per person
$389
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Villa 1565

Villa 1565

3 out of 5
Price was $455, price is now $333 per person
$333
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Price was $469, price is now $351 per person
$351
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

4-night Anastasia Island vacations

Price found within the past 48 hours. Click for updated prices.
The Irlo

The Irlo

3 out of 5
Save 100% on your flight
Price was $341, price is now $229 per person
$229
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,182, price is now $468 per person
$468
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $876, price is now $449 per person
$449
per person
Oct 15 - Oct 19
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
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 $1,256, price is now $663 per person
$663
per person
Oct 13 - Oct 17
found 1 day 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 $520, price is now $284 per person
$284
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $459, price is now $263 per person
$263
per person
Oct 13 - Oct 17
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 $886, price is now $510 per person
$510
per person
Oct 23 - Oct 27
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 $622, price is now $366 per person
$366
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $480, price is now $283 per person
$283
per person
Oct 16 - Oct 20
found 23 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Amelia by the South

Amelia by the South

4.5 out of 5
Save 100% on your flight
Price was $5,815, price is now $3,586 per person
$3,586
per person
Oct 9 - Oct 13
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $407, price is now $269 per person
$269
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Summer Bay Orlando MOD Collection by Sonesta

Summer Bay Orlando MOD Collection by Sonesta

3.5 out of 5
Save 100% on your flight
Price was $422, price is now $280 per person
$280
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

5-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 $620, price is now $323 per person
$323
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,218, price is now $355 per person
$355
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,053, price is now $493 per person
$493
per person
Oct 14 - Oct 19
found 22 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
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 $1,744, price is now $905 per person
$905
per person
Oct 14 - Oct 19
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 $1,122, price is now $614 per person
$614
per person
Oct 20 - Oct 25
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 $846, price is now $466 per person
$466
per person
Oct 14 - Oct 19
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $597, price is now $356 per person
$356
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $1,099, price is now $682 per person
$682
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

2.5 out of 5
Save 100% on your flight
Price was $779, price is now $502 per person
$502
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $658, price is now $429 per person
$429
per person
Oct 14 - Oct 19
found 22 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Save 100% on your flight
Price was $1,184, price is now $776 per person
$776
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
ette hotel

ette hotel

5 out of 5
Save 100% on your flight
Price was $1,866, price is now $1,225 per person
$1,225
per person
Oct 25 - Oct 30
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

6-7 night Anastasia Island vacations

Price found within the past 48 hours. Click for updated prices.
The Irlo

The Irlo

3 out of 5
Save 100% on your flight
Price was $464, price is now $307 per person
$307
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,813, price is now $660 per person
$660
per person
Oct 8 - Oct 15
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 $857, price is now $411 per person
$411
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $807, price is now $389 per person
$389
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
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 $2,513, price is now $1,344 per person
$1,344
per person
Oct 8 - Oct 15
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 $981, price is now $530 per person
$530
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

2.5 out of 5
Save 100% on your flight
Price was $817, price is now $465 per person
$465
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
Price was $1,054, price is now $631 per person
$631
per person
Oct 16 - Oct 22
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,575, price is now $967 per person
$967
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $1,326, price is now $822 per person
$822
per person
Oct 19 - Oct 25
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 $1,186, price is now $754 per person
$754
per person
Oct 11 - Oct 17
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 $596, price is now $382 per person
$382
per person
Oct 25 - Oct 31
found 20 hours ago
Roundtrip non-stop 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.

Mon, Oct 26 - Fri, Oct 30
TTN
Trenton
MCO
Orlando
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Trenton to Orlando, returning Fri, Oct 30, priced at $89 found 1 day ago
Sun, Oct 11 - Fri, Oct 16
DTW
Detroit
MCO
Orlando
$105 Roundtrip, found 3 days ago
$105
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Oct 11 from Detroit to Orlando, returning Fri, Oct 16, priced at $105 found 3 days ago
Mon, Nov 16 - Fri, Nov 20
PHL
Philadelphia
MCO
Orlando
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 16 from Philadelphia to Orlando, returning Fri, Nov 20, priced at $113 found 1 day 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
$134 nightly
The price is $150 total per night
$150 total
Sep 7 - Sep 8
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 St. Augustine Beach and 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
$98 nightly
The price is $109 total per night
$109 total
Sep 13 - Sep 14
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
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
$96 nightly
The price is $107 total per night
$107 total
Sep 7 - Sep 8
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.
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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.

Top Picks

^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.