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.
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $1,594, price is now $958 per person
$958
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
Price was $477, price is now $309 per person
$309
per person
Jan 28 - Jan 31
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 $1,661, price is now $989 per person
$989
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,594, price is now $958 per person
$958
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,010, price is now $640 per person
$640
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip 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 $967, price is now $617 per person
$617
per person
Jan 16 - Jan 19
found 11 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
Save 100% on your flight
Price was $1,076, price is now $689 per person
$689
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $668, price is now $444 per person
$444
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $722, price is now $492 per person
$492
per person
Jan 16 - Jan 19
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
Save 100% on your flight
Price was $901, price is now $618 per person
$618
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $633, price is now $435 per person
$435
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $594, price is now $414 per person
$414
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 $637, price is now $448 per person
$448
per person
Jan 16 - Jan 19
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 $604, price is now $369 per person
$369
per person
Jan 16 - Jan 20
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 $882, price is now $436 per person
$436
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
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 $2,164, price is now $1,314 per person
$1,314
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,574, price is now $1,032 per person
$1,032
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
Price was $792, price is now $524 per person
$524
per person
Jan 21 - Jan 25
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $959, price is now $656 per person
$656
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,128, price is now $793 per person
$793
per person
Jan 28 - Feb 1
found 13 hours 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 $1,198, price is now $844 per person
$844
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $900, price is now $640 per person
$640
per person
Jan 16 - Jan 20
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 $1,069, price is now $764 per person
$764
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Landing Palmetto Apartments

Landing Palmetto Apartments

4 out of 5
Save 100% on your flight
Price was $1,012, price is now $727 per person
$727
per person
Jan 28 - Feb 1
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,038, price is now $752 per person
$752
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

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
Save 100% on your flight
Price was $682, price is now $367 per person
$367
per person
Jan 18 - Jan 23
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,237, price is now $518 per person
$518
per person
Jan 27 - Feb 1
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
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
Price was $2,928, price is now $1,604 per person
$1,604
per person
Feb 5 - Feb 10
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,372, price is now $789 per person
$789
per person
Jan 20 - Jan 25
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,017 per person
$1,017
per person
Feb 5 - Feb 10
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,926, price is now $1,179 per person
$1,179
per person
Feb 5 - Feb 10
found 12 hours 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 $1,304, price is now $806 per person
$806
per person
Feb 5 - Feb 10
found 13 hours 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 $1,254, price is now $814 per person
$814
per person
Feb 5 - Feb 10
found 13 hours ago
Roundtrip non-stop 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 $835, price is now $547 per person
$547
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,067, price is now $714 per person
$714
per person
Feb 3 - Feb 8
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,603, price is now $1,092 per person
$1,092
per person
Feb 5 - Feb 10
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

6-7 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 $795, price is now $413 per person
$413
per person
Jan 18 - Jan 24
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,589, price is now $582 per person
$582
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip 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
Save 100% on your flight
Price was $1,343, price is now $603 per person
$603
per person
Feb 7 - Feb 14
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $3,186, price is now $1,714 per person
$1,714
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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 $2,636, price is now $1,479 per person
$1,479
per person
Jan 31 - Feb 6
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 $1,576, price is now $902 per person
$902
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $2,137, price is now $1,258 per person
$1,258
per person
Feb 7 - Feb 14
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
Save 100% on your flight
Price was $1,644, price is now $980 per person
$980
per person
Jan 31 - Feb 6
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 $1,265, price is now $763 per person
$763
per person
Jan 24 - Jan 31
just found
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $976, price is now $592 per person
$592
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $2,331, price is now $1,418 per person
$1,418
per person
Feb 7 - Feb 14
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $1,098, price is now $680 per person
$680
per person
Jan 24 - Jan 31
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, Jan 18 - Wed, Jan 21
EWR
New York
SRQ
Sarasota
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select United flight, departing Sun, Jan 18 from New York to Sarasota, returning Wed, Jan 21, priced at $129 found 2 days ago
Tue, Jan 20 - Fri, Jan 23
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jan 20 from Boston to Sarasota, returning Fri, Jan 23, priced at $137 found 1 day ago
Sun, Jan 11 - Sat, Jan 17
PHL
Philadelphia
SRQ
Sarasota
$194 Roundtrip, found 14 hours ago
$194
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Jan 11 from Philadelphia to Sarasota, returning Sat, Jan 17, priced at $194 found 14 hours 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
$212 nightly
The price is $240 total per night
$240 total
Dec 18 - Dec 19
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
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
$138 nightly
The price is $156 total per night
$156 total
Dec 18 - Dec 19
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
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
2200 Gulf Dr N Bradenton Beach FL
Free Cancellation
Reserve now, pay when you stay
1.93 mi from city center
$676 nightly
The price is $764 total per night
$764 total
Dec 22 - Dec 23
Total with taxes and fees
When you stay at Seaside at Anna Maria Island Inn in Bradenton Beach, you'll be on the beach, within a 15-minute drive of Coquina Beach and Anna Maria Beach.
Pool
Free WiFi
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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.