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Anna Maria Island Vacation Packages

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Anna Maria Island Flight + Hotel Packages

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

Kompose Boutique Hotel

3 out of 5
Price was $791, price is now $562 per person
$562
per person
Aug 14 - Aug 21
found 16 hours 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 Mote Marine Laboratory & Aquarium are located nearby.
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,889, price is now $1,121 per person
$1,121
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,069, price is now $709 per person
$709
per person
Aug 14 - Aug 21
found 16 hours 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.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,264, price is now $1,542 per person
$1,542
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,661, price is now $1,145 per person
$1,145
per person
Jul 15 - Jul 20
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 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 $1,032, price is now $725 per person
$725
per person
Aug 14 - Aug 21
found 17 hours 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 BC Resort on the Water

The BC Resort on the Water

4 out of 5
Price was $1,073, price is now $760 per person
$760
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in St. Petersburg. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
The Capri at Siesta

The Capri at Siesta

3 out of 5
Save 100% on your flight
Price was $1,346, price is now $957 per person
$957
per person
Aug 14 - Aug 21
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Anna Maria Island Vacation Packages 3-4 Night Stays

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

The Westin Sarasota

4 out of 5
Central Sarasota
Price was $782, price is now $550 per person
$550
per person
Aug 12 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,889, price is now $1,121 per person
$1,121
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,264, price is now $1,542 per person
$1,542
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,521, price is now $1,046 per person
$1,046
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

Anna Maria Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $1,404, price is now $898 per person
$898
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Price was $2,601, price is now $1,325 per person
$1,325
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,985, price is now $1,149 per person
$1,149
per person
Aug 14 - Aug 21
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $2,189, price is now $1,452 per person
$1,452
per person
Jul 6 - Jul 12
found 1 day ago
Roundtrip non-stop 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.

American Airlines
Tue, Nov 10 - Wed, Nov 18
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 10 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 18, priced at $237 found 1 day ago
Delta
Sat, Sep 26 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 30, priced at $239 found 1 day ago
American Airlines
Tue, Jul 21 - Tue, Jul 28
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 21 from Logan Intl. to Sarasota-Bradenton Intl., returning Tue, Jul 28, priced at $242 found 1 day ago
United
Tue, Oct 20 - Thu, Nov 19
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$259 Roundtrip, found 20 hours ago
$259
Roundtrip
found 20 hours ago
Select United flight, departing Tue, Oct 20 from Detroit Metropolitan Wayne County to Sarasota-Bradenton Intl., returning Thu, Nov 19, priced at $259 found 20 hours ago