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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $5,141, price is now $2,947 per person
$2,947
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was $5,886, price is now $3,639 per person
$3,639
per person
Mar 21 - Mar 28
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.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Price was $480, price is now $356 per person
$356
per person
Feb 27 - Mar 2
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $587, price is now $379 per person
$379
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,184, price is now $794 per person
$794
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $831, price is now $561 per person
$561
per person
Mar 15 - Mar 18
found 1 day ago
Roundtrip non-stop 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 $2,034, price is now $1,412 per person
$1,412
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
The Beachview Inn Clearwater Beach

The Beachview Inn Clearwater Beach

3 out of 5
Save 100% on your flight
Price was $788, price is now $556 per person
$556
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
Price was $1,388, price is now $990 per person
$990
per person
Mar 2 - Mar 5
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 $755, price is now $548 per person
$548
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,931, price is now $1,408 per person
$1,408
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $882, price is now $647 per person
$647
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,028, price is now $763 per person
$763
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,443, price is now $1,076 per person
$1,076
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop 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 $691, price is now $444 per person
$444
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,386, price is now $1,581 per person
$1,581
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,457, price is now $990 per person
$990
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $2,751, price is now $1,940 per person
$1,940
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Arvilla

Arvilla

2 out of 5
Save 100% on your flight
Price was $828, price is now $588 per person
$588
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,286, price is now $926 per person
$926
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Sarasota (SRQ)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Price was $1,870, price is now $1,369 per person
$1,369
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
Price was $878, price is now $648 per person
$648
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,379, price is now $1,028 per person
$1,028
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
John's Pass Hotel

John's Pass Hotel

2 out of 5
Save 100% on your flight
Price was $921, price is now $687 per person
$687
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Peninsula Bed & Cocktails

Peninsula Bed & Cocktails

3.5 out of 5
Save 100% on your flight
Price was $893, price is now $669 per person
$669
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Residence Inn by Marriott Sarasota Bradenton

Residence Inn by Marriott Sarasota Bradenton

3 out of 5
Price was $1,040, price is now $783 per person
$783
per person
Mar 16 - Mar 20
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

5-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
Price was $704, price is now $347 per person
$347
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $3,055, price is now $2,031 per person
$2,031
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,094, price is now $1,442 per person
$1,442
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,442, price is now $1,012 per person
$1,012
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,281, price is now $2,340 per person
$2,340
per person
Mar 6 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Arvilla

Arvilla

2 out of 5
Save 100% on your flight
Price was $1,056, price is now $757 per person
$757
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
Price was $1,646, price is now $1,188 per person
$1,188
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,483, price is now $1,081 per person
$1,081
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,301, price is now $948 per person
$948
per person
Mar 6 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hampton Inn & Suites Sarasota/Bradenton-Airport, FL

Hampton Inn & Suites Sarasota/Bradenton-Airport, FL

2.5 out of 5
Save 100% on your flight
Price was $1,261, price is now $922 per person
$922
per person
Feb 27 - Mar 4
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,468, price is now $1,085 per person
$1,085
per person
Mar 6 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $1,327, price is now $990 per person
$990
per person
Mar 6 - Mar 11
found 1 day 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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,099, price is now $669 per person
$669
per person
Mar 11 - Mar 17
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
Price was $5,141, price is now $2,947 per person
$2,947
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,669, price is now $990 per person
$990
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,454, price is now $881 per person
$881
per person
Mar 21 - Mar 28
found 1 day 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 $2,485, price is now $1,522 per person
$1,522
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was $5,886, price is now $3,639 per person
$3,639
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,680, price is now $1,057 per person
$1,057
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,299 per person
$1,299
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,873, price is now $1,226 per person
$1,226
per person
Mar 15 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,422, price is now $939 per person
$939
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $3,170, price is now $2,108 per person
$2,108
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $2,224, price is now $1,488 per person
$1,488
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Flight deals to Anna Maria Island

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

Sun, Feb 15 - Tue, Feb 17
PHL
Philadelphia
SRQ
Sarasota
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Feb 15 from Philadelphia to Sarasota, returning Tue, Feb 17, priced at $139 found 5 days ago
Sat, Feb 21 - Fri, Feb 27
EWR
New York
SRQ
Sarasota
$149 Roundtrip, found 2 days ago
$149
Roundtrip
found 2 days ago
Select United flight, departing Sat, Feb 21 from New York to Sarasota, returning Fri, Feb 27, priced at $149 found 2 days ago
Thu, Feb 19 - Sat, Feb 21
ATL
Atlanta
SRQ
Sarasota
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Atlanta to Sarasota, returning Sat, Feb 21, priced at $151 found 3 days ago

Top rated hotels for your Anna Maria Island vacation

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
202 1st St N Bradenton Beach FL
2.83 mi from city center
$422 nightly
The price is $476 total per night
$476 total
Jan 30 - Jan 31
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.
Pool
Hot Tub
Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

2.5 out of 5
1325 Gulf Drive North Bradenton Beach FL
2.28 mi from city center
Get rates
With a stay at Tortuga Inn Beach Resort in Bradenton Beach, you'll be near the beach, steps from Bradenton Beach and a 5-minute drive from Coquina Beach.
Pool
Parking included
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
6900 Gulf Dr Holmes Beach FL
0.86 mi from city center
$395 nightly
The price is $447 total per night
$447 total
Feb 1 - Feb 2
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.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Anna Maria Island
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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.