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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.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $638, price is now $438 per person
$438
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,509, price is now $867 per person
$867
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Save 100% on your flight
Price was $4,559, price is now $2,748 per person
$2,748
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Stay at this villa in Palm Harbor. Enjoy free WiFi, free parking, and a garden. Popular attractions Curlew Crossing Shopping Center and Dunedin Golf Club are located nearby.
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,465, price is now $945 per person
$945
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Beach Walk and Pier 60 Park are located nearby.
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $927, price is now $606 per person
$606
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this beach resort in St. Pete Beach. Enjoy a full-service spa, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,288, price is now $877 per person
$877
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Save 100% on your flight
Price was $911, price is now $631 per person
$631
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this beach aparthotel in Indian Shores. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Petersburg - Clearwater Beaches and John's Pass Village & Boardwalk are located nearby.
Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $748 per person
$748
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Madison (MSN) to Tampa (TPA)
Stay at this aparthotel in Dunedin. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Anna Maria Island Vacation Packages 3-4 Night Stays

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

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $927, price is now $606 per person
$606
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,509, price is now $867 per person
$867
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,465, price is now $945 per person
$945
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Save 100% on your flight
Price was $2,944, price is now $1,916 per person
$1,916
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)

Anna Maria Island 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 $1,104, price is now $644 per person
$644
per person
Jul 19 - Jul 24
found 5 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,779, price is now $965 per person
$965
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Save 100% on your flight
Price was $4,559, price is now $2,748 per person
$2,748
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,090 per person
$1,090
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)

Top Flight Deals

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

Delta
Sat, Sep 26 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 30, priced at $219 found 1 hour ago
Delta
Tue, Jul 21 - Tue, Jul 28
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$222 Roundtrip, found 6 hours ago
$222
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Jul 21 from Logan Intl. to Sarasota-Bradenton Intl., returning Tue, Jul 28, priced at $222 found 6 hours ago
United
Tue, Oct 20 - Thu, Nov 19
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days 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 2 days ago
American Airlines
Tue, Nov 10 - Wed, Nov 18
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$261 Roundtrip, found 13 hours ago
$261
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Nov 10 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 18, priced at $261 found 13 hours ago