Cheap Vacations in Anna Maria Island

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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 20 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 22 hours ago
Roundtrip flight included
Boston (BOS) 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 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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)
La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

4 out of 5
Price was $946, price is now $727 per person
$727
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Capri at Siesta

The Capri at Siesta

3 out of 5
Price was $686, price is now $530 per person
$530
per person
Jul 20 - Jul 23
found 3 hours 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.
Last Hoorah

Last Hoorah

2.5 out of 5
Price was $554, price is now $404 per person
$404
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip 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 $1,447, price is now $913 per person
$913
per person
Jul 23 - Jul 27
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 $1,391, price is now $918 per person
$918
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip 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)
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,245, price is now $854 per person
$854
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip 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)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,761, price is now $1,906 per person
$1,906
per person
Jul 23 - Jul 27
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)
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 15 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,226, price is now $887 per person
$887
per person
Jul 24 - Jul 28
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 $1,117, price is now $817 per person
$817
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

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 $889, price is now $527 per person
$527
per person
Jul 20 - Jul 25
found 21 hours 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 $1,557, price is now $947 per person
$947
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip 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 15 hours 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)
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 15 hours 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)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,450, price is now $1,007 per person
$1,007
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 $1,089, price is now $758 per person
$758
per person
Aug 5 - Aug 10
found 15 hours 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.
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 11 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 23 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,046, price is now $738 per person
$738
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $892, price is now $636 per person
$636
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,154, price is now $825 per person
$825
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Landing Bradenton Near G.T. Bray Park

Landing Bradenton Near G.T. Bray Park

4 out of 5
Save 100% on your flight
Price was $1,422, price is now $1,035 per person
$1,035
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $1,048, price is now $769 per person
$769
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Carlisle Inn

Carlisle Inn

3.5 out of 5
Price was $1,066, price is now $799 per person
$799
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Little Gull Cottages by Coolvacay

Little Gull Cottages by Coolvacay

3 out of 5
Price was $1,466, price is now $1,120 per person
$1,120
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $805, price is now $616 per person
$616
per person
Aug 1 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 21 hours ago
$197
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Fri, Aug 21 from Boston to Sarasota, returning Mon, Aug 24, priced at $197 found 21 hours ago
Sat, Sep 26 - Wed, Sep 30
ORD
Chicago
SRQ
Sarasota
$234 Roundtrip, found 13 hours ago
$234
Roundtrip
found 13 hours ago
Select United flight, departing Sat, Sep 26 from Chicago to Sarasota, returning Wed, Sep 30, priced at $234 found 13 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
$205 nightly
The price is $232 total per night
$232 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.