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Anna Maria Vacation Packages

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A sunset over the ocean with a clear sky and calm waters.

Anna Maria
Florida
United States of America
North America
Hotwire.com

Anna Maria Flight + Hotel Packages

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

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5

Save 100% on your flight

Price was $688, price is now $436 per person

$436

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $1,360, price is now $833 per person

$833

per person

Dec 1 - Dec 5

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.

voco Sarasota by IHG

3.5 out of 5

Save 100% on your flight

Price was $1,452, price is now $936 per person

$936

per person

Dec 8 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

It was very comfortable. I love the fact you have transportation to go to the beach and that you gave us the umbrella, towels and chairs. The front desk personnel were very nice and helpful. Thanks

Reviewed on Sep 23, 2026

The Avalon Club

4 out of 5

Save 100% on your flight

Price was $1,412, price is now $925 per person

$925

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Our family had a wonderful stay. The location was perfect. We also loved being able to use the hotels umbrellas, chairs & towels at the beach. The suite was more spacious than we expected! The sofa bed was not comfortable, but the regular beds were. Can’t beat the price for the room & view we had. We would absolutely come back!

Reviewed on Sep 21, 2026

Seaside at Anna Maria Island Inn

3 out of 5

Save 100% on your flight

Price was $3,066, price is now $2,034 per person

$2,034

per person

Dec 8 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach hotel in Bradenton Beach. Enjoy a beach locale, daily housekeeping, and cable TV channels. Popular attractions Coquina Beach and Bradenton Beach are located nearby.

Great place to stay! Friendly staff and beautiful ocean front rooms.

Reviewed on Sep 18, 2026

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,497, price is now $999 per person

$999

per person

Dec 16 - Dec 21

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.

It was very nice. My husband is ready to return

Reviewed on Sep 23, 2026

VIinoy House

3.5 out of 5

Save 100% on your flight

Price was $1,230, price is now $826 per person

$826

per person

Nov 9 - Nov 15

found 3 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

Stay at this B&B in St. Petersburg. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Tampa Bay and Vinoy Park are located nearby.

The Westin Sarasota

4 out of 5

Save 100% on your flight

Price was $2,013, price is now $1,358 per person

$1,358

per person

Nov 13 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.