Cheap Vacations in Anna Maria Island

Choose two or more items and save on your trip:

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
Price was $589, price is now $256 per person
$256
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $1,625, price is now $937 per person
$937
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $769, price is now $480 per person
$480
per person
Feb 19 - Feb 22
found 20 hours ago
Roundtrip non-stop 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 $757, price is now $491 per person
$491
per person
Feb 2 - Feb 5
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
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 $735, price is now $479 per person
$479
per person
Feb 2 - Feb 5
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $636, price is now $433 per person
$433
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $783, price is now $546 per person
$546
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $993, price is now $698 per person
$698
per person
Feb 7 - Feb 10
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 $693, price is now $492 per person
$492
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
Save 100% on your flight
Price was $780, price is now $556 per person
$556
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $613, price is now $446 per person
$446
per person
Feb 10 - Feb 13
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $605, price is now $445 per person
$445
per person
Feb 10 - Feb 13
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
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 $882, price is now $496 per person
$496
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Save 100% on your flight
Price was $926, price is now $508 per person
$508
per person
Feb 12 - Feb 16
found 11 hours ago
Roundtrip non-stop 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
Price was $2,683, price is now $1,627 per person
$1,627
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $1,181, price is now $788 per person
$788
per person
Feb 12 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,026, price is now $692 per person
$692
per person
Feb 10 - Feb 14
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Price was $1,149, price is now $784 per person
$784
per person
Feb 6 - Feb 10
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,516, price is now $1,040 per person
$1,040
per person
Feb 13 - Feb 17
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

2 out of 5
Save 100% on your flight
Price was $2,516, price is now $1,738 per person
$1,738
per person
Feb 13 - Feb 17
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,314, price is now $915 per person
$915
per person
Feb 12 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,512, price is now $1,081 per person
$1,081
per person
Feb 10 - Feb 14
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Candlewood Suites Safety Harbor - Clearwater NE by IHG

Candlewood Suites Safety Harbor - Clearwater NE by IHG

2.5 out of 5
Price was $753, price is now $539 per person
$539
per person
Feb 12 - Feb 16
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 $1,261, price is now $905 per person
$905
per person
Feb 13 - Feb 17
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $682, price is now $310 per person
$310
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,536, price is now $899 per person
$899
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Save 100% on your flight
Price was $1,017, price is now $601 per person
$601
per person
Jan 24 - Jan 29
found 9 hours ago
Roundtrip flight included
Chicago (ORD) 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 $2,532, price is now $1,532 per person
$1,532
per person
Jan 24 - Jan 29
found 9 hours ago
Roundtrip flight included
Chicago (ORD) 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 $915, price is now $582 per person
$582
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,067, price is now $692 per person
$692
per person
Jan 24 - Jan 29
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,057, price is now $686 per person
$686
per person
Jan 24 - Jan 29
found 9 hours 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 $1,726, price is now $1,131 per person
$1,131
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $940, price is now $618 per person
$618
per person
Jan 24 - Jan 29
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Save 100% on your flight
Price was $741, price is now $493 per person
$493
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $882, price is now $597 per person
$597
per person
Jan 24 - Jan 29
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,453, price is now $984 per person
$984
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Safety Harbor - Clearwater NE by IHG

Candlewood Suites Safety Harbor - Clearwater NE by IHG

2.5 out of 5
Save 100% on your flight
Price was $688, price is now $431 per person
$431
per person
Feb 16 - Feb 23
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $1,369, price is now $564 per person
$564
per person
Feb 16 - Feb 23
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Save 100% on your flight
Price was $1,582, price is now $934 per person
$934
per person
Feb 16 - Feb 23
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,958, price is now $1,179 per person
$1,179
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $1,297, price is now $803 per person
$803
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,468, price is now $915 per person
$915
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Landing Palmetto Apartments

Landing Palmetto Apartments

4 out of 5
Price was $1,413, price is now $895 per person
$895
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Price was $1,498, price is now $954 per person
$954
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was $1,134, price is now $731 per person
$731
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Price was $1,321, price is now $859 per person
$859
per person
Feb 7 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,096, price is now $716 per person
$716
per person
Feb 16 - Feb 23
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Save 100% on your flight
Price was $1,290, price is now $844 per person
$844
per person
Feb 8 - Feb 14
found 21 hours ago
Roundtrip flight included
Detroit (DTW) 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.

Sat, Jan 31 - Sat, Feb 7
EWR
New York
SRQ
Sarasota
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 31 from New York to Sarasota, returning Sat, Feb 7, priced at $129 found 1 day ago
Tue, Jan 27 - Wed, Jan 28
JFK
New York
SRQ
Sarasota
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jan 27 from New York to Sarasota, returning Wed, Jan 28, priced at $130 found 2 days ago
Thu, Feb 5 - Mon, Feb 9
BOS
Boston
SRQ
Sarasota
$154 Roundtrip, found 3 hours ago
$154
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Feb 5 from Boston to Sarasota, returning Mon, Feb 9, priced at $154 found 3 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
$329 nightly
The price is $372 total per night
$372 total
Jan 8 - Jan 9, 2026
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
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
$752 nightly
The price is $850 total per night
$850 total
Jan 21 - Jan 22, 2026
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
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
$357 nightly
The price is $403 total per night
$403 total
Jan 5 - Jan 6, 2026
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
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.