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Anna Maria Vacation Packages

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Anna Maria Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Save 100% on your flight
Price was $727, price is now $510 per person
$510
per person
Dec 24 - Dec 27
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly B&B in Tampa. Enjoy free WiFi, free parking, and 3 meeting rooms. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,514, price is now $869 per person
$869
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $2,682, price is now $1,732 per person
$1,732
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The rooms are very nice and clean. There is a pleasant aroma when you enter the building and all through the resort. The food is excellent with excellent prices. I would definitely stay again.

Reviewed on Oct 2, 2026

Inn on the Beach - 18+ only

Inn on the Beach - 18+ only

2.5 out of 5
Save 100% on your flight
Price was $904, price is now $601 per person
$601
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this beach motel in St. Pete Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Fort De Soto Park and Hurley Park are located nearby.

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,205, price is now $809 per person
$809
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
Best place to stay on island!

Reviewed on Oct 1, 2026

4BR Spacious Paradise

4BR Spacious Paradise

3 out of 5
Save 100% on your flight
Price was $1,462, price is now $986 per person
$986
per person
Nov 9 - Nov 16
found 21 hours ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Stay at this apartment in Siesta Key. Enjoy free parking, a garden, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Calini Beach Club by Coolvacay

Calini Beach Club by Coolvacay

3 out of 5
Save 100% on your flight
Price was $2,247, price is now $1,564 per person
$1,564
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this condo in Siesta Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

2.5 out of 5
Price was $1,573, price is now $1,110 per person
$1,110
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Dunedin. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Excellent location , immaculate modern rooms , lovely little private pool. Highly recommended

Reviewed on Oct 2, 2026

Anna Maria Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Hyde Park
Save 100% on your flight
Price was $727, price is now $510 per person
$510
per person
Dec 24 - Dec 27
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,910, price is now $1,858 per person
$1,858
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,205, price is now $809 per person
$809
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $912, price is now $619 per person
$619
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Anna Maria Vacation Packages 5-7 Night Stays

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 $1,167, price is now $763 per person
$763
per person
Dec 5 - Dec 12
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
Sunshine Beach
Save 100% on your flight
Price was $1,514, price is now $869 per person
$869
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $2,682, price is now $1,732 per person
$1,732
per person
Dec 25 - Dec 31
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 $1,952, price is now $1,275 per person
$1,275
per person
Nov 23 - Nov 28
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Mon, Nov 2 - Mon, Nov 16
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$93 Roundtrip, found 3 days ago
$93
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Mon, Nov 2 from Philadelphia Intl. to St. Petersburg-Clearwater Intl., returning Mon, Nov 16, priced at $93 found 3 days ago
Frontier Airlines
Mon, Nov 9 - Tue, Nov 10
CLE
Hopkins Intl.
TPA
Tampa Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Hopkins Intl. to Tampa Intl., returning Tue, Nov 10, priced at $104 found 2 days ago
Frontier Airlines
Tue, Dec 1 - Wed, Dec 16
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$116 Roundtrip, found 1 hour ago
$116
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Detroit Metropolitan Wayne County to Tampa Intl., returning Wed, Dec 16, priced at $116 found 1 hour ago
Allegiant Air
Sun, Oct 18 - Thu, Nov 5
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sun, Oct 18 from Mercer to St. Petersburg-Clearwater Intl., returning Thu, Nov 5, priced at $134 found 3 days ago