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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,218, price is now $763 per person
$763
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) 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 $1,377, price is now $969 per person
$969
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,302, price is now $956 per person
$956
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $3,151, price is now $2,350 per person
$2,350
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $578, price is now $420 per person
$420
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Stones Throw Beachfront Luxury Suites

Stones Throw Beachfront Luxury Suites

2 out of 5
Save 100% on your flight
Price was $1,556, price is now $1,241 per person
$1,241
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $779, price is now $622 per person
$622
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $750, price is now $613 per person
$613
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,308, price is now $832 per person
$832
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,208 per person
$1,208
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,296, price is now $911 per person
$911
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $747, price is now $562 per person
$562
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Akron (CAK) 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)
The Luce, St. Pete Beach, a Tribute Portfolio Hotel

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

4 out of 5
Price was $855, price is now $650 per person
$650
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Washington (IAD) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,012, price is now $782 per person
$782
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $873, price is now $630 per person
$630
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,209, price is now $776 per person
$776
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,055, price is now $1,363 per person
$1,363
per person
Jul 17 - Jul 21
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,526, price is now $1,044 per person
$1,044
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,528, price is now $1,069 per person
$1,069
per person
Jul 24 - Jul 28
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $1,377, price is now $969 per person
$969
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,002, price is now $711 per person
$711
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,335, price is now $969 per person
$969
per person
Jul 17 - Jul 21
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,302, price is now $956 per person
$956
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $908, price is now $669 per person
$669
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,574, price is now $1,160 per person
$1,160
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) 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 $3,151, price is now $2,350 per person
$2,350
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

5-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
Save 100% on your flight
Price was $489, price is now $329 per person
$329
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $718, price is now $431 per person
$431
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,218, price is now $763 per person
$763
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) 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 $927, price is now $602 per person
$602
per person
Aug 2 - Aug 7
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
Save 100% on your flight
Price was $687, price is now $448 per person
$448
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $867, price is now $570 per person
$570
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,276, price is now $1,502 per person
$1,502
per person
Jul 13 - Jul 18
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $3,804, price is now $2,550 per person
$2,550
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $996, price is now $682 per person
$682
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,172, price is now $804 per person
$804
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Akron (CAK) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Save 100% on your flight
Price was $1,576, price is now $1,087 per person
$1,087
per person
Jul 24 - Jul 29
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,667, price is now $1,151 per person
$1,151
per person
Jul 13 - Jul 18
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
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 19 hours ago
Roundtrip non-stop flight included
Akron (CAK) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,366, price is now $1,204 per person
$1,204
per person
Jul 18 - Jul 25
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $2,135, price is now $1,305 per person
$1,305
per person
Jul 18 - Jul 25
found 24 hours 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 $2,024, price is now $1,284 per person
$1,284
per person
Jul 18 - Jul 25
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,157, price is now $2,037 per person
$2,037
per person
Jul 18 - Jul 25
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $4,293, price is now $2,774 per person
$2,774
per person
Jul 18 - Jul 25
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $1,430, price is now $946 per person
$946
per person
Jul 18 - Jul 25
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $2,163, price is now $1,435 per person
$1,435
per person
Jul 18 - Jul 25
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,334, price is now $928 per person
$928
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,068, price is now $757 per person
$757
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The BC Resort on the Water

The BC Resort on the Water

4 out of 5
Save 100% on your flight
Price was $1,057, price is now $755 per person
$755
per person
Jul 24 - Jul 31
found 1 day ago
Roundtrip flight included
Providence (PVD) to Tampa (TPA)
Inn on the Beach

Inn on the Beach

2.5 out of 5
Save 100% on your flight
Price was $1,919, price is now $1,380 per person
$1,380
per person
Jul 17 - Jul 23
found 1 day ago
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.

Fri, Aug 14 - Mon, Aug 17
BOS
Boston
SRQ
Sarasota
$197 Roundtrip, found 9 hours ago
$197
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Fri, Aug 14 from Boston to Sarasota, returning Mon, Aug 17, priced at $197 found 9 hours ago
Sat, Sep 19 - Wed, Sep 23
ORD
Chicago
SRQ
Sarasota
$234 Roundtrip, found 11 hours ago
$234
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Sep 19 from Chicago to Sarasota, returning Wed, Sep 23, priced at $234 found 11 hours ago
Sun, Jul 12 - Tue, Jul 14
ATL
Atlanta
SRQ
Sarasota
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jul 12 from Atlanta to Sarasota, returning Tue, Jul 14, priced at $244 found 1 day 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 15 - Jun 16
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.