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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.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $974, price is now $568 per person
$568
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,461, price is now $871 per person
$871
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $2,664, price is now $1,603 per person
$1,603
per person
Mar 28 - Apr 4
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.
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was $4,608, price is now $2,802 per person
$2,802
per person
Apr 1 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 Bean Point Beach are located nearby.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,554, price is now $954 per person
$954
per person
Apr 26 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. 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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,011, price is now $631 per person
$631
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 Coquina Beach and Bean Point Beach are located nearby.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $2,143, price is now $1,376 per person
$1,376
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip 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.
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $984, price is now $636 per person
$636
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, 3 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Anna Maria Vacation Packages 3-4 Night Stays

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

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $696, price is now $447 per person
$447
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $974, price is now $568 per person
$568
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,011, price is now $631 per person
$631
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $761, price is now $478 per person
$478
per person
Apr 9 - Apr 13
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

Anna Maria Vacation Packages 5-7 Night Stays

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

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,177, price is now $659 per person
$659
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,461, price is now $871 per person
$871
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $2,664, price is now $1,603 per person
$1,603
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was $4,608, price is now $2,802 per person
$2,802
per person
Apr 1 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

Top Flight Deals

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

Frontier Airlines
Sat, May 9 - Fri, May 15
ORD
O'Hare Intl.
TPA
Tampa Intl.
$58 Roundtrip, found 4 hours ago
$58
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from O'Hare Intl. to Tampa Intl., returning Fri, May 15, priced at $58 found 4 hours ago
Frontier Airlines
Tue, Apr 21 - Tue, Apr 28
CLE
Hopkins Intl.
TPA
Tampa Intl.
$78 Roundtrip, found 1 hour ago
$78
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 21 from Hopkins Intl. to Tampa Intl., returning Tue, Apr 28, priced at $78 found 1 hour ago
Frontier Airlines
Mon, Apr 13 - Thu, Apr 16
TTN
Mercer
TPA
Tampa Intl.
$78 Roundtrip, found 23 hours ago
$78
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Apr 13 from Mercer to Tampa Intl., returning Thu, Apr 16, priced at $78 found 23 hours ago
Frontier Airlines
Tue, Apr 14 - Thu, Apr 16
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$82 Roundtrip, found 6 hours ago
$82
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Philadelphia Intl. to Tampa Intl., returning Thu, Apr 16, priced at $82 found 6 hours ago