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.
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
Price was $296, price is now $208 per person
$208
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
Save 100% on your flight
Price was $592, price is now $357 per person
$357
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,187, price is now $777 per person
$777
per person
Oct 30 - Nov 2
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $456, price is now $299 per person
$299
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $556, price is now $374 per person
$374
per person
Nov 7 - Nov 10
found 18 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $805, price is now $544 per person
$544
per person
Oct 30 - Nov 2
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $598, price is now $408 per person
$408
per person
Oct 30 - Nov 2
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $708, price is now $487 per person
$487
per person
Oct 30 - Nov 2
found 11 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $777, price is now $547 per person
$547
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Blue Wave Suites

Blue Wave Suites

2 out of 5
Save 100% on your flight
Price was $511, price is now $360 per person
$360
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $463, price is now $329 per person
$329
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flight
Price was $438, price is now $313 per person
$313
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
BAY INN

BAY INN

2 out of 5
Price was $319, price is now $230 per person
$230
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
Save 100% on your flight
Price was $793, price is now $506 per person
$506
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Save 100% on your flight
Price was $633, price is now $413 per person
$413
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Comfort Inn & Suites Bradenton North I-75

Comfort Inn & Suites Bradenton North I-75

2.5 out of 5
Save 100% on your flight
Price was $499, price is now $334 per person
$334
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,733, price is now $1,174 per person
$1,174
per person
Oct 29 - Nov 2
found 8 hours ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $834, price is now $566 per person
$566
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $714, price is now $488 per person
$488
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $645, price is now $444 per person
$444
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $5,093, price is now $3,559 per person
$3,559
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Tampa (TPA)
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
Price was $573, price is now $410 per person
$410
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $633, price is now $453 per person
$453
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Sleep Inn & Suites St Petersburg Gateway

Sleep Inn & Suites St Petersburg Gateway

3 out of 5
Price was $369, price is now $264 per person
$264
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
Price was $721, price is now $499 per person
$499
per person
Oct 28 - Nov 2
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $780 per person
$780
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,061, price is now $679 per person
$679
per person
Oct 28 - Nov 2
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
Price was $912, price is now $613 per person
$613
per person
Oct 28 - Nov 2
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Tampa (TPA)
Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Save 100% on your flight
Price was $735, price is now $501 per person
$501
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Turtle Beach Resort

Turtle Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,204, price is now $825 per person
$825
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,099, price is now $755 per person
$755
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,224 per person
$1,224
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $941, price is now $653 per person
$653
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
4BR Spacious Paradise

4BR Spacious Paradise

3 out of 5
Save 100% on your flight
Price was $1,191, price is now $828 per person
$828
per person
Oct 22 - Oct 27
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $834, price is now $585 per person
$585
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Carlisle Inn

Carlisle Inn

3.5 out of 5
Save 100% on your flight
Price was $909, price is now $643 per person
$643
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)

6-7 night Anna Maria Island vacations

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

Westwinds Waterfront Resort

3 out of 5
Save 100% on your flight
Price was $860, price is now $512 per person
$512
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,381, price is now $727 per person
$727
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,003, price is now $1,180 per person
$1,180
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,101, price is now $659 per person
$659
per person
Oct 17 - Oct 24
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,070, price is now $694 per person
$694
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,335, price is now $870 per person
$870
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $916, price is now $602 per person
$602
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
Price was $830, price is now $549 per person
$549
per person
Oct 17 - Oct 24
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $1,144, price is now $759 per person
$759
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
Price was $960, price is now $644 per person
$644
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,138, price is now $765 per person
$765
per person
Oct 17 - Oct 24
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
Price was $950, price is now $640 per person
$640
per person
Oct 23 - Oct 30
found 4 hours ago
Roundtrip flight included
Columbus (CMH) 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, Oct 2 - Mon, Oct 5
PHL
Philadelphia
PIE
St. Petersburg
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Oct 2 from Philadelphia to St. Petersburg, returning Mon, Oct 5, priced at $78 found 6 days ago
Sun, Oct 11 - Thu, Oct 15
TTN
Trenton
PIE
St. Petersburg
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Sun, Oct 11 from Trenton to St. Petersburg, returning Thu, Oct 15, priced at $111 found 4 days ago
Thu, Dec 10 - Sun, Dec 13
SWF
Newburgh
PIE
St. Petersburg
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Dec 10 from Newburgh to St. Petersburg, returning Sun, Dec 13, priced at $181 found 3 days ago

Top rated hotels for your Anna Maria Island vacation

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
6306 Gulf Dr Holmes Beach FL
0.62 mi from city center
$444 nightly
The price is $502 total per night
$502 total
Sep 29 - Sep 30
Total with taxes and fees
With a stay at Anna Maria Beach Resort in Holmes Beach, you'll be a 1-minute drive from Bradenton Beach and 6 minutes from Anna Maria Beach.
On private beach
Pool
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
6900 Gulf Dr Holmes Beach FL
0.86 mi from city center
$427 nightly
The price is $483 total per night
$483 total
Oct 12 - Oct 13
Total with taxes and fees
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, a 1-minute drive from Bradenton Beach and 5 minutes from Bean Point Beach.
Pool
Spa
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
$195 nightly
The price is $220 total per night
$220 total
Sep 22 - Sep 23
Total with taxes and fees
When you stay at The Retreat at Anna Maria Island Inn in Bradenton Beach, you'll be near the beach, a 3-minute drive from Bradenton Beach and 6 minutes from Coquina Beach.
Pool
Pet friendly
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.