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 $3,117, price is now $2,083 per person
$2,083
per person
Mar 16 - Mar 20
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 $530, price is now $314 per person
$314
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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)
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)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,390, price is now $1,007 per person
$1,007
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,363, price is now $1,735 per person
$1,735
per person
Mar 5 - Mar 8
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
Price was $1,103, price is now $811 per person
$811
per person
Mar 13 - Mar 16
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)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Price was $1,078, price is now $807 per person
$807
per person
Mar 7 - Mar 10
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
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)

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 $681, price is now $432 per person
$432
per person
Mar 14 - Mar 18
found 7 hours 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 $1,180, price is now $783 per person
$783
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 $3,117, price is now $2,083 per person
$2,083
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip 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 $1,362, price is now $928 per person
$928
per person
Mar 12 - Mar 16
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 $1,766, price is now $1,240 per person
$1,240
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,620, price is now $1,139 per person
$1,139
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $2,276, price is now $1,605 per person
$1,605
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $965, price is now $692 per person
$692
per person
Mar 16 - Mar 20
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 $1,166, price is now $839 per person
$839
per person
Mar 16 - Mar 20
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 $1,146, price is now $842 per person
$842
per person
Mar 18 - Mar 22
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

2 out of 5
Price was $1,607, price is now $1,190 per person
$1,190
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,462, price is now $1,086 per person
$1,086
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 1 day 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 1 day 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 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,839, price is now $921 per person
$921
per person
Mar 11 - Mar 18
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
Price was $1,066, price is now $538 per person
$538
per person
Mar 14 - Mar 21
found 6 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $1,221, price is now $724 per person
$724
per person
Feb 28 - Mar 6
found 9 hours 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 $1,370, price is now $827 per person
$827
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $1,197, price is now $736 per person
$736
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $2,583, price is now $1,642 per person
$1,642
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,440, price is now $924 per person
$924
per person
Mar 11 - Mar 18
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 $942, price is now $607 per person
$607
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Price was $1,989, price is now $1,291 per person
$1,291
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
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)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,631, price is now $1,085 per person
$1,085
per person
Mar 1 - Mar 7
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 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 18 from Atlanta to Sarasota, returning Sat, Feb 21, priced at $142 found 1 day 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
$329 nightly
The price is $372 total per night
$372 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.