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 $1,997, price is now $1,018 per person
$1,018
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,319 per person
$1,319
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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
Price was $561, price is now $351 per person
$351
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,266, price is now $672 per person
$672
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $978, price is now $579 per person
$579
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Longboat Bay Club

Longboat Bay Club

3.5 out of 5
Save 100% on your flight
Price was $1,102, price is now $673 per person
$673
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $1,385, price is now $881 per person
$881
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Save 100% on your flight
Price was $729, price is now $471 per person
$471
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Hyatt Place Sarasota Lakewood Ranch

Hyatt Place Sarasota Lakewood Ranch

3 out of 5
Save 100% on your flight
Price was $897, price is now $589 per person
$589
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Sarasota (SRQ)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $621, price is now $413 per person
$413
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG

2.5 out of 5
Save 100% on your flight
Price was $579, price is now $385 per person
$385
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $544, price is now $364 per person
$364
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,032, price is now $699 per person
$699
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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 $596, price is now $324 per person
$324
per person
Jan 21 - Jan 25
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $1,903, price is now $1,143 per person
$1,143
per person
Jan 8 - Jan 12
found 2 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,762, price is now $1,074 per person
$1,074
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Sirata St. Pete Beach

Sirata St. Pete Beach

3 out of 5
Save 100% on your flight
Price was $612, price is now $379 per person
$379
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,519, price is now $942 per person
$942
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Residence Inn by Marriott Tampa Westshore/Airport

Residence Inn by Marriott Tampa Westshore/Airport

3 out of 5
Save 100% on your flight
Price was $761, price is now $486 per person
$486
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $838, price is now $546 per person
$546
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $926, price is now $612 per person
$612
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,031, price is now $683 per person
$683
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $977, price is now $648 per person
$648
per person
Jan 8 - Jan 12
found 2 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Gemma by Brightwild

The Gemma by Brightwild

5 out of 5
Save 100% on your flight
Price was $5,407, price is now $3,719 per person
$3,719
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,127, price is now $776 per person
$776
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Sarasota East - I-75 by IHG

Holiday Inn Express Sarasota East - I-75 by IHG

2.5 out of 5
Save 100% on your flight
Price was $696, price is now $393 per person
$393
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,997, price is now $1,018 per person
$1,018
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,171, price is now $622 per person
$622
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $904, price is now $495 per person
$495
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
Longboat Bay Club

Longboat Bay Club

3.5 out of 5
Price was $1,644, price is now $913 per person
$913
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $896, price is now $498 per person
$498
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,241, price is now $710 per person
$710
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $796, price is now $456 per person
$456
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,396, price is now $812 per person
$812
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $2,728, price is now $1,592 per person
$1,592
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,079, price is now $638 per person
$638
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Sarasota (SRQ)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Sirata St. Pete Beach

Sirata St. Pete Beach

3 out of 5
Save 100% on your flight
Price was $822, price is now $485 per person
$485
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $1,142, price is now $609 per person
$609
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,024, price is now $564 per person
$564
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $977, price is now $545 per person
$545
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $3,026, price is now $1,718 per person
$1,718
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,128, price is now $656 per person
$656
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,032 per person
$1,032
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,714, price is now $1,005 per person
$1,005
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $1,097, price is now $644 per person
$644
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,820, price is now $1,661 per person
$1,661
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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 $1,340, price is now $795 per person
$795
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,592, price is now $965 per person
$965
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Fri, Jan 9 - Mon, Jan 12
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Boston to Sarasota, returning Mon, Jan 12, priced at $137 found 2 days ago
Sat, Jan 10 - Sat, Jan 17
ORD
Chicago
SRQ
Sarasota
$145 Roundtrip, found 10 hours ago
$145
Roundtrip
found 10 hours ago
Select United flight, departing Sat, Jan 10 from Chicago to Sarasota, returning Sat, Jan 17, priced at $145 found 10 hours ago
Sun, Jan 25 - Wed, Feb 4
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Jan 25 from New York to Sarasota, returning Wed, Feb 4, priced at $147 found 6 days 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
0.87 mi from city center
$408 nightly
The price is $461 total per night
$461 total
Dec 10 - Dec 11
Total with taxes and fees
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, within a 10-minute drive of Bean Point Beach and Anna Maria Beach.
Pool
Spa
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
1.36 mi from city center
$178 nightly
The price is $202 total per night
$202 total
Dec 8 - Dec 9
Total with taxes and fees
When you stay at Haley's at The Anna Maria Island Inn in Holmes Beach, you'll be by the ocean, within a 5-minute drive of Bean Point Beach and Manatee Public Beach.
Pool
Pet friendly
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
$250 nightly
The price is $282 total per night
$282 total
Dec 7 - Dec 8
Total with taxes and fees
When you stay at Pelican Post at Anna Maria Island Inn in Bradenton Beach, you'll be in the entertainment district, within a 15-minute drive of Coquina Beach and Anna Maria Beach.
Pool
Hot Tub
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.