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.
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $601, price is now $487 per person
$487
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $947, price is now $693 per person
$693
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $799, price is now $587 per person
$587
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Price was $910, price is now $674 per person
$674
per person
Sep 4 - Sep 7
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
Price was $1,022, price is now $770 per person
$770
per person
Sep 4 - Sep 7
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
Price was $727, price is now $558 per person
$558
per person
Sep 5 - Sep 8
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Price was $785, price is now $606 per person
$606
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $3,653, price is now $2,845 per person
$2,845
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $736, price is now $574 per person
$574
per person
Aug 29 - Sep 1
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
Price was $1,198, price is now $943 per person
$943
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Price was $709, price is now $575 per person
$575
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

3 out of 5
Price was $1,130, price is now $924 per person
$924
per person
Sep 4 - Sep 7
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.
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Price was $641, price is now $486 per person
$486
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip 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 $1,438, price is now $902 per person
$902
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip 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
Save 100% on your flight
Price was $821, price is now $569 per person
$569
per person
Sep 2 - Sep 6
found 23 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 $1,124, price is now $788 per person
$788
per person
Sep 10 - Sep 14
found 10 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,011, price is now $715 per person
$715
per person
Aug 28 - Sep 1
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 $1,159, price is now $831 per person
$831
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $4,737, price is now $3,457 per person
$3,457
per person
Sep 10 - Sep 14
found 10 hours ago
Roundtrip flight included
Indianapolis (IND) to Tampa (TPA)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Price was $875, price is now $643 per person
$643
per person
Sep 2 - Sep 6
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $957, price is now $711 per person
$711
per person
Sep 2 - Sep 6
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $869, price is now $655 per person
$655
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Price was $757, price is now $580 per person
$580
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
SkyBeach Resort

SkyBeach Resort

4 out of 5
Price was $982, price is now $753 per person
$753
per person
Sep 3 - Sep 7
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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $593, price is now $426 per person
$426
per person
Sep 3 - Sep 8
found 21 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 $1,820, price is now $948 per person
$948
per person
Sep 3 - Sep 8
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,021, price is now $600 per person
$600
per person
Sep 14 - Sep 19
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,126, price is now $741 per person
$741
per person
Sep 14 - Sep 19
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $792, price is now $530 per person
$530
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip 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 $1,285, price is now $880 per person
$880
per person
Sep 14 - Sep 19
found 10 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 $1,104, price is now $766 per person
$766
per person
Sep 14 - Sep 19
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $632, price is now $446 per person
$446
per person
Sep 3 - Sep 8
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,174, price is now $833 per person
$833
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was $904, price is now $642 per person
$642
per person
Sep 14 - Sep 19
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Casa Limonada Boutique Motel

Casa Limonada Boutique Motel

3.5 out of 5
Save 100% on your flight
Price was $1,729, price is now $1,237 per person
$1,237
per person
Sep 10 - Sep 15
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Carlisle Inn

Carlisle Inn

3.5 out of 5
Save 100% on your flight
Price was $997, price is now $713 per person
$713
per person
Sep 4 - Sep 9
found 1 day 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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $740, price is now $542 per person
$542
per person
Sep 11 - Sep 17
found 16 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 $1,553, price is now $901 per person
$901
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,577, price is now $954 per person
$954
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,402, price is now $871 per person
$871
per person
Aug 28 - Sep 4
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 $1,983, price is now $1,291 per person
$1,291
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop 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 $1,913, price is now $1,270 per person
$1,270
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was $1,073, price is now $713 per person
$713
per person
Sep 6 - Sep 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,111, price is now $755 per person
$755
per person
Sep 6 - Sep 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,680, price is now $1,156 per person
$1,156
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Price was $967, price is now $682 per person
$682
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $891, price is now $632 per person
$632
per person
Sep 11 - Sep 17
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Oasis Palms

Oasis Palms

2 out of 5
Price was $844, price is now $604 per person
$604
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
New York (JFK) 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.

Thu, Oct 29 - Sun, Nov 1
TTN
Trenton
PIE
St. Petersburg
$78 Roundtrip, found 12 hours ago
$78
Roundtrip
found 12 hours ago
Select Allegiant Air flight, departing Thu, Oct 29 from Trenton to St. Petersburg, returning Sun, Nov 1, priced at $78 found 12 hours ago
Fri, Oct 30 - Mon, Nov 2
PHL
Philadelphia
PIE
St. Petersburg
$78 Roundtrip, found 10 hours ago
$78
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Fri, Oct 30 from Philadelphia to St. Petersburg, returning Mon, Nov 2, priced at $78 found 10 hours ago
Thu, Sep 3 - Sun, Sep 6
SWF
Newburgh
PIE
St. Petersburg
$110 Roundtrip, found 8 hours ago
$110
Roundtrip
found 8 hours ago
Select Allegiant Air flight, departing Thu, Sep 3 from Newburgh to St. Petersburg, returning Sun, Sep 6, priced at $110 found 8 hours 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
$297 nightly
The price is $335 total per night
$335 total
Aug 20 - Aug 21
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.
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
$214 nightly
The price is $242 total per night
$242 total
Aug 25 - Aug 26
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.
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
202 1st St N Bradenton Beach FL
2.83 mi from city center
$236 nightly
The price is $267 total per night
$267 total
Aug 27 - Aug 28
Total with taxes and fees
With a stay at Pelican Post at Anna Maria Island Inn in Bradenton Beach, you'll be in the entertainment district, a 3-minute walk from Bradenton Beach and 7 minutes by foot from Cortez Beach.
Pool
Hot Tub
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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.