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.
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
Price was $1,409, price is now $1,010 per person
$1,010
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,521, price is now $1,098 per person
$1,098
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)

3-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 $581, price is now $368 per person
$368
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop 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 $1,309, price is now $843 per person
$843
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Save 100% on your flight
Price was $731, price is now $472 per person
$472
per person
Feb 22 - Feb 25
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,533, price is now $1,013 per person
$1,013
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $762, price is now $504 per person
$504
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $626, price is now $417 per person
$417
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $774, price is now $529 per person
$529
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $609, price is now $420 per person
$420
per person
Feb 23 - Feb 26
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
Save 100% on your flight
Price was $703, price is now $489 per person
$489
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,254, price is now $873 per person
$873
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $972, price is now $677 per person
$677
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Clearwater Beach Sheraton Resort on Sand Key

Clearwater Beach Sheraton Resort on Sand Key

4 out of 5
Save 100% on your flight
Price was $957, price is now $672 per person
$672
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

4-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 $438, price is now $280 per person
$280
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $536, price is now $311 per person
$311
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,186, price is now $719 per person
$719
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

Fairfield Inn & Suites by Marriott Sarasota Lakewood Ranch

2.5 out of 5
Save 100% on your flight
Price was $760, price is now $480 per person
$480
per person
Feb 23 - Feb 27
found 21 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $849, price is now $538 per person
$538
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $767, price is now $486 per person
$486
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $901, price is now $598 per person
$598
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,114, price is now $769 per person
$769
per person
Mar 3 - Mar 7
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,330, price is now $921 per person
$921
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
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 $2,332, price is now $1,624 per person
$1,624
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
Price was $492, price is now $345 per person
$345
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $962, price is now $676 per person
$676
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

5-night Anna Maria Island vacations

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

Weathered The Storm

3 out of 5
Save 100% on your flight
Price was $478, price is now $276 per person
$276
per person
Mar 1 - Mar 6
found 16 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,383, price is now $683 per person
$683
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,187, price is now $642 per person
$642
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,553, price is now $887 per person
$887
per person
Feb 27 - Mar 4
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 $1,026, price is now $600 per person
$600
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,333, price is now $794 per person
$794
per person
Mar 8 - Mar 13
found 8 hours ago
Roundtrip flight included
Cleveland (CLE) 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 $1,059, price is now $647 per person
$647
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,188, price is now $726 per person
$726
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,160, price is now $1,327 per person
$1,327
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,360, price is now $842 per person
$842
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $905, price is now $566 per person
$566
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,001, price is now $630 per person
$630
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

6-7 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
Save 100% on your flight
Price was $1,387, price is now $822 per person
$822
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,766, price is now $920 per person
$920
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,622, price is now $940 per person
$940
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,208, price is now $1,292 per person
$1,292
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,391, price is now $839 per person
$839
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $2,358, price is now $1,447 per person
$1,447
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,561, price is now $959 per person
$959
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Sarasota (SRQ)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,481, price is now $910 per person
$910
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,576, price is now $969 per person
$969
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $1,455, price is now $902 per person
$902
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,811, price is now $1,131 per person
$1,131
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,883, price is now $1,804 per person
$1,804
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.

Mon, Feb 2 - Tue, Feb 3
JFK
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Mon, Feb 2 - Tue, Feb 3
EWR
New York
SRQ
Sarasota
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Mon, Feb 2 from New York to Sarasota, returning Tue, Feb 3, priced at $157 found 1 day ago
Fri, Jan 30 - Sat, Jan 31
LGA
New York
SRQ
Sarasota
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 30 from New York to Sarasota, returning Sat, Jan 31, priced at $177 found 1 day ago

Top rated hotels for your Anna Maria Island vacation

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
$263 nightly
The price is $297 total per night
$297 total
Jan 19 - Jan 20
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
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
8102 Gulf Drive Holmes Beach FL
1.35 mi from city center
$144 nightly
The price is $163 total per night
$163 total
Jan 19 - Jan 20
Total with taxes and fees
Located in Holmes Beach, Haley's at The Anna Maria Island Inn is by the ocean, a 4-minute drive from Bean Point Beach and 6 minutes from Manatee Public Beach.
Pool
Pet friendly
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
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.