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.
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $2,814, price is now $1,766 per person
$1,766
per person
Jan 23 - Jan 29
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Last Hoorah

Last Hoorah

2.5 out of 5
Save 100% on your flight
Price was $235, price is now $155 per person
$155
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $672, price is now $295 per person
$295
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $2,012, price is now $1,164 per person
$1,164
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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 $1,558, price is now $938 per person
$938
per person
Jan 23 - Jan 26
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Venice Beach Villas

Venice Beach Villas

3 out of 5
Save 100% on your flight
Price was $497, price is now $304 per person
$304
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Weathered The Storm

Weathered The Storm

3 out of 5
Save 100% on your flight
Price was $303, price is now $188 per person
$188
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Price was $816, price is now $509 per person
$509
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,010, price is now $634 per person
$634
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $573, price is now $363 per person
$363
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,294, price is now $819 per person
$819
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $926, price is now $619 per person
$619
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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 $790, price is now $533 per person
$533
per person
Jan 23 - Jan 26
found 2 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)

4-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 $905, price is now $455 per person
$455
per person
Jan 29 - Feb 2
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $2,593, price is now $1,471 per person
$1,471
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,256, price is now $759 per person
$759
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,149, price is now $746 per person
$746
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $785, price is now $526 per person
$526
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $982, price is now $670 per person
$670
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $647, price is now $458 per person
$458
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,039, price is now $736 per person
$736
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $911, price is now $646 per person
$646
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $683, price is now $492 per person
$492
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,905, price is now $1,379 per person
$1,379
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $918, price is now $620 per person
$620
per person
Jan 25 - Jan 30
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Price was $3,396, price is now $1,784 per person
$1,784
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) 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 $2,446, price is now $1,394 per person
$1,394
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,334, price is now $827 per person
$827
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $692 per person
$692
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,106, price is now $720 per person
$720
per person
Jan 25 - Jan 30
found 23 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Price was $1,131, price is now $753 per person
$753
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,503, price is now $1,005 per person
$1,005
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) 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 $1,207, price is now $810 per person
$810
per person
Jan 30 - Feb 4
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $1,134, price is now $779 per person
$779
per person
Jan 27 - Feb 1
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $907, price is now $629 per person
$629
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Save 100% on your flight
Price was $791, price is now $522 per person
$522
per person
Jan 13 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,398, price is now $544 per person
$544
per person
Jan 13 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $3,394, price is now $1,861 per person
$1,861
per person
Jan 18 - Jan 25
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,161, price is now $665 per person
$665
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $1,043, price is now $644 per person
$644
per person
Jan 23 - Jan 29
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) 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 $2,814, price is now $1,766 per person
$1,766
per person
Jan 23 - Jan 29
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
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 $1,114, price is now $701 per person
$701
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Venice Beach Villas

Venice Beach Villas

3 out of 5
Save 100% on your flight
Price was $1,118, price is now $713 per person
$713
per person
Jan 18 - Jan 25
found 1 hour ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,186, price is now $775 per person
$775
per person
Jan 23 - Jan 29
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) 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 $1,235, price is now $809 per person
$809
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,274, price is now $840 per person
$840
per person
Jan 23 - Jan 29
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,218, price is now $807 per person
$807
per person
Jan 19 - Jan 25
just found
Roundtrip flight included
Chicago (ORD) 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 1 day ago
$129
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jan 18 from New York to Sarasota, returning Wed, Jan 21, priced at $129 found 1 day ago
Sun, Jan 25 - Wed, Feb 4
JFK
New York
SRQ
Sarasota
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Jan 25 from New York to Sarasota, returning Wed, Feb 4, priced at $137 found 4 days ago
Fri, Jan 16 - Tue, Jan 20
LGA
New York
SRQ
Sarasota
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jan 16 from New York to Sarasota, returning Tue, Jan 20, priced at $160 found 4 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
$250 nightly
The price is $282 total per night
$282 total
Dec 15 - Dec 16
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
$148 nightly
The price is $167 total per night
$167 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
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
$289 nightly
The price is $327 total per night
$327 total
Dec 14 - Dec 15
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
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.