Cheap Vacations in Anna Maria Island

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Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Price was $695, price is now $527 per person
$527
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,954, price is now $1,780 per person
$1,780
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,213, price is now $816 per person
$816
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $477, price is now $348 per person
$348
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,213, price is now $816 per person
$816
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $772, price is now $523 per person
$523
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $837, price is now $606 per person
$606
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Azul Resort Siesta Key

Azul Resort Siesta Key

3 out of 5
Save 100% on your flight
Price was $888, price is now $643 per person
$643
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Price was $656, price is now $477 per person
$477
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $834, price is now $607 per person
$607
per person
Apr 29 - May 2
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $741, price is now $541 per person
$541
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $3,940, price is now $2,911 per person
$2,911
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Hemingway

The Hemingway

4 out of 5
Save 100% on your flight
Price was $946, price is now $700 per person
$700
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $584, price is now $434 per person
$434
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $708, price is now $459 per person
$459
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,954, price is now $1,780 per person
$1,780
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,941, price is now $1,326 per person
$1,326
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $1,454, price is now $1,031 per person
$1,031
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,441, price is now $1,022 per person
$1,022
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,306, price is now $934 per person
$934
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,149, price is now $834 per person
$834
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was $1,528, price is now $1,117 per person
$1,117
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,006, price is now $743 per person
$743
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,983, price is now $2,218 per person
$2,218
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Price was $2,141, price is now $1,610 per person
$1,610
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $715, price is now $523 per person
$523
per person
May 3 - May 8
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,016, price is now $1,298 per person
$1,298
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $982, price is now $642 per person
$642
per person
May 3 - May 8
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,361, price is now $937 per person
$937
per person
May 3 - May 8
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $963, price is now $667 per person
$667
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $1,613, price is now $1,128 per person
$1,128
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Price was $1,102, price is now $772 per person
$772
per person
Apr 28 - May 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,093, price is now $769 per person
$769
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,275, price is now $906 per person
$906
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,799, price is now $1,299 per person
$1,299
per person
May 3 - May 8
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $1,564, price is now $1,133 per person
$1,133
per person
Apr 21 - Apr 26
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $902, price is now $537 per person
$537
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,728, price is now $1,699 per person
$1,699
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $3,947, price is now $2,538 per person
$2,538
per person
Apr 14 - Apr 20
just found
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $1,987, price is now $1,320 per person
$1,320
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $1,470, price is now $984 per person
$984
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,669, price is now $1,146 per person
$1,146
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,842, price is now $1,273 per person
$1,273
per person
Apr 23 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $3,411, price is now $2,413 per person
$2,413
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $2,020, price is now $1,444 per person
$1,444
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,438, price is now $1,033 per person
$1,033
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,048, price is now $1,503 per person
$1,503
per person
Apr 22 - Apr 29
just found
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

Flight deals to Anna Maria Island

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

Sun, Apr 5 - Thu, Apr 9
BOS
Boston
SRQ
Sarasota
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Apr 5 from Boston to Sarasota, returning Thu, Apr 9, priced at $197 found 4 days ago
Fri, Apr 10 - Thu, Apr 16
JFK
New York
SRQ
Sarasota
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Apr 10 from New York to Sarasota, returning Thu, Apr 16, priced at $222 found 5 days ago
Mon, Jul 20 - Mon, Jul 27
EWR
New York
SRQ
Sarasota
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select United flight, departing Mon, Jul 20 from New York to Sarasota, returning Mon, Jul 27, priced at $227 found 3 days ago

Top rated hotels for your Anna Maria Island vacation

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
6900 Gulf Dr Holmes Beach FL
0.86 mi from city center
$694 nightly
The price is $784 total per night
$784 total
Mar 11 - Mar 12
Total with taxes and fees
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the waterfront, a 1-minute drive from Bradenton Beach and 5 minutes from Bean Point Beach.
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
202 1st St N Bradenton Beach FL
2.83 mi from city center
$819 nightly
The price is $926 total per night
$926 total
Mar 25 - Mar 26
Total with taxes and fees
With a stay at Pelican Post at Anna Maria Island Inn in Bradenton Beach, you'll be in the entertainment district, a 3-minute walk from Bradenton Beach and a 4-minute drive from Coquina Beach.
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3 out of 5
2218 Gulf Drive N Bradenton Beach FL
1.86 mi from city center
$496 nightly
The price is $560 total per night
$560 total
Mar 11 - Mar 12
Total with taxes and fees
When you stay at Seabreeze at Anna Maria Island Inn in Bradenton Beach, you'll be on the beach, a 1-minute drive from Bradenton Beach and 5 minutes from Coquina Beach.
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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.