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.
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,128, price is now $758 per person
$758
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,207, price is now $785 per person
$785
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,908, price is now $2,026 per person
$2,026
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

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 $607, price is now $396 per person
$396
per person
Jul 15 - Jul 18
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Price was $1,098, price is now $689 per person
$689
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,630, price is now $1,108 per person
$1,108
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Price was $1,177, price is now $810 per person
$810
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,033, price is now $758 per person
$758
per person
Aug 7 - Aug 10
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $974, price is now $724 per person
$724
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $601, price is now $451 per person
$451
per person
Jul 17 - Jul 20
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $630, price is now $475 per person
$475
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $852, price is now $642 per person
$642
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Luce, St. Pete Beach, a Tribute Portfolio Hotel

The Luce, St. Pete Beach, a Tribute Portfolio Hotel

4 out of 5
Price was $747, price is now $565 per person
$565
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Price was $811, price is now $617 per person
$617
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $709, price is now $540 per person
$540
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $535, price is now $382 per person
$382
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,327, price is now $810 per person
$810
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,207, price is now $785 per person
$785
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,020, price is now $1,354 per person
$1,354
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,128, price is now $758 per person
$758
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,483, price is now $1,018 per person
$1,018
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $877, price is now $608 per person
$608
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,908, price is now $2,026 per person
$2,026
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $1,010, price is now $705 per person
$705
per person
Aug 5 - Aug 9
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 $655, price is now $460 per person
$460
per person
Aug 5 - Aug 9
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 $820, price is now $585 per person
$585
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Inn on the Beach

Inn on the Beach

2.5 out of 5
Save 100% on your flight
Price was $1,358, price is now $972 per person
$972
per person
Jul 16 - Jul 20
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $762, price is now $519 per person
$519
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $889, price is now $527 per person
$527
per person
Jul 20 - Jul 25
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,524, price is now $913 per person
$913
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,428, price is now $876 per person
$876
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,301, price is now $1,475 per person
$1,475
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,324, price is now $874 per person
$874
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $806, price is now $552 per person
$552
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Luce, St. Pete Beach, a Tribute Portfolio Hotel

The Luce, St. Pete Beach, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,091, price is now $747 per person
$747
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $1,185, price is now $816 per person
$816
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $3,449, price is now $2,380 per person
$2,380
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $967, price is now $667 per person
$667
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,726, price is now $1,194 per person
$1,194
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Tropical Palms Hotel

Tropical Palms Hotel

2.5 out of 5
Price was $580, price is now $466 per person
$466
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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 $1,203, price is now $696 per person
$696
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $2,024, price is now $1,284 per person
$1,284
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,233, price is now $863 per person
$863
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Palm Cove Motel

Palm Cove Motel

2 out of 5
Price was $675, price is now $515 per person
$515
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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
Price was $793, price is now $607 per person
$607
per person
Jul 15 - Jul 22
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $8,890, price is now $6,809 per person
$6,809
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

3 out of 5
Price was $727, price is now $574 per person
$574
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $2,495, price is now $1,974 per person
$1,974
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Country Inn & Suites by Radisson, St. Petersburg - Clearwater, FL

Country Inn & Suites by Radisson, St. Petersburg - Clearwater, FL

3 out of 5
Price was $708, price is now $561 per person
$561
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Four Bed Home With Pool Game Room Bar Near Beach

Four Bed Home With Pool Game Room Bar Near Beach

2 out of 5
Save 100% on your flight
Price was $2,441, price is now $1,934 per person
$1,934
per person
Jul 20 - Jul 27
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Hampton Inn & Suites Tampa Northwest/Oldsmar

Hampton Inn & Suites Tampa Northwest/Oldsmar

2.5 out of 5
Price was $839, price is now $665 per person
$665
per person
Jul 15 - Jul 22
found 5 hours ago
Roundtrip flight included
Dallas (DFW) 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.

Fri, Aug 21 - Mon, Aug 24
BOS
Boston
SRQ
Sarasota
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Fri, Aug 21 from Boston to Sarasota, returning Mon, Aug 24, priced at $197 found 15 hours ago
Sat, Sep 26 - Wed, Sep 30
ORD
Chicago
SRQ
Sarasota
$234 Roundtrip, found 7 hours ago
$234
Roundtrip
found 7 hours ago
Select United flight, departing Sat, Sep 26 from Chicago to Sarasota, returning Wed, Sep 30, priced at $234 found 7 hours ago
Sun, Jul 12 - Tue, Jul 14
ATL
Atlanta
SRQ
Sarasota
$244 Roundtrip, found 2 days ago
$244
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Jul 12 from Atlanta to Sarasota, returning Tue, Jul 14, priced at $244 found 2 days ago

Top rated hotels for your Anna Maria Island vacation

Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
101 22nd St Bradenton Beach FL
Free Cancellation
Reserve now, pay when you stay
1.98 mi from city center
$228 nightly
The price is $258 total per night
$258 total
Jun 16 - Jun 17
Total with taxes and fees
With a stay at Tropic Isle at Anna Maria Island Inn in Bradenton Beach, you'll be by the ocean, steps from Bradenton Beach and a 3-minute drive from Cortez Beach.
Pool
Pet friendly
The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

2 out of 5
2305 Gulf Dr N Bradenton Beach FL
1.83 mi from city center
$194 nightly
The price is $219 total per night
$219 total
Jun 15 - Jun 16
Total with taxes and fees
With a stay at The Retreat at Anna Maria Island Inn in Bradenton Beach, you'll be near the beach, steps from Bradenton Beach and a 3-minute drive from Cortez 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.

Top Picks

^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.