Cheap Vacations in Anna Maria Island

Choose two or more items and save on your trip:

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
Save 100% on your flight
Price was $4,862, price is now $3,168 per person
$3,168
per person
Feb 28 - Mar 7
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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $562, price is now $375 per person
$375
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $905, price is now $598 per person
$598
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $907, price is now $631 per person
$631
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,554, price is now $1,790 per person
$1,790
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $789, price is now $554 per person
$554
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop 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
Price was $1,295, price is now $966 per person
$966
per person
Mar 5 - Mar 8
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 $2,615, price is now $1,950 per person
$1,950
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $860, price is now $646 per person
$646
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop 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 $1,178, price is now $885 per person
$885
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Price was $582, price is now $442 per person
$442
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Price was $672, price is now $512 per person
$512
per person
Mar 15 - Mar 18
found 21 hours ago
Roundtrip non-stop 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 $1,570, price is now $1,198 per person
$1,198
per person
Mar 19 - Mar 22
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

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 $693, price is now $452 per person
$452
per person
Mar 23 - Mar 27
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
Save 100% on your flight
Price was $1,017, price is now $663 per person
$663
per person
Mar 16 - Mar 20
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 $1,050, price is now $703 per person
$703
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $848, price is now $572 per person
$572
per person
Mar 16 - Mar 20
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 $2,503, price is now $1,691 per person
$1,691
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 $1,796, price is now $1,220 per person
$1,220
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $874, price is now $598 per person
$598
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,536, price is now $1,056 per person
$1,056
per person
Mar 7 - Mar 11
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
Save 100% on your flight
Price was $1,038, price is now $719 per person
$719
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,497, price is now $1,750 per person
$1,750
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,342, price is now $966 per person
$966
per person
Mar 16 - Mar 20
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
Save 100% on your flight
Price was $905, price is now $663 per person
$663
per person
Mar 16 - Mar 20
found 1 day 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.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Save 100% on your flight
Price was $479, price is now $272 per person
$272
per person
Mar 1 - Mar 6
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,235, price is now $652 per person
$652
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $905, price is now $538 per person
$538
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,555, price is now $941 per person
$941
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $849, price is now $514 per person
$514
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,042, price is now $647 per person
$647
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,211, price is now $1,376 per person
$1,376
per person
Mar 8 - Mar 13
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,175, price is now $744 per person
$744
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 $1,309, price is now $842 per person
$842
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,035, price is now $671 per person
$671
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
Save 100% on your flight
Price was $767, price is now $507 per person
$507
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop 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.
Lemon Bay Motel

Lemon Bay Motel

2 out of 5
Save 100% on your flight
Price was $752, price is now $455 per person
$455
per person
Mar 17 - Mar 24
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $1,066, price is now $538 per person
$538
per person
Mar 14 - Mar 21
found 2 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,708, price is now $1,026 per person
$1,026
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,551, price is now $958 per person
$958
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,093, price is now $678 per person
$678
per person
Mar 11 - Mar 18
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 $2,471, price is now $1,549 per person
$1,549
per person
Mar 5 - Mar 12
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 $1,840, price is now $1,163 per person
$1,163
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,261, price is now $1,443 per person
$1,443
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,496, price is now $960 per person
$960
per person
Feb 28 - Mar 7
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 $4,862, price is now $3,168 per person
$3,168
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip 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 $1,878, price is now $1,235 per person
$1,235
per person
Feb 28 - Mar 7
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 $2,649, price is now $1,746 per person
$1,746
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop 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.

Wed, Feb 18 - Sat, Feb 21
ATL
Atlanta
SRQ
Sarasota
$142 Roundtrip, found 20 hours ago
$142
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Wed, Feb 18 from Atlanta to Sarasota, returning Sat, Feb 21, priced at $142 found 20 hours ago
Sat, Feb 21 - Fri, Feb 27
EWR
New York
SRQ
Sarasota
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select United flight, departing Sat, Feb 21 from New York to Sarasota, returning Fri, Feb 27, priced at $149 found 3 days ago
Mon, Feb 9 - Tue, Feb 10
BOS
Boston
SRQ
Sarasota
$152 Roundtrip, found 6 days ago
$152
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Feb 9 from Boston to Sarasota, returning Tue, Feb 10, priced at $152 found 6 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
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.