Anna Maria Island Vacation Packages for 2026

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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
Price was $901, price is now $684 per person
$684
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Easy check in. Nice staff. Beautiful hotel

Reviewed on Nov 2, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,507, price is now $1,050 per person
$1,050
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) 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.

CW Resort

CW Resort

4 out of 5
Price was $1,117, price is now $794 per person
$794
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) 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.
Amazing property and value! We will be back!

Reviewed on Nov 2, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,099, price is now $783 per person
$783
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) 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.

The Avalon Club

The Avalon Club

4 out of 5
Price was $1,372, price is now $984 per person
$984
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) 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.

Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Sunshine Beach
Price was $5,609, price is now $4,293 per person
$4,293
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
Islip (ISP) to Tampa (TPA)
Stay at this apartment in Treasure Island. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

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Top Hotel Deals

The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

2 out of 5
2305 Gulf Dr N Bradenton Beach FL
2.94 km from city center
Stay at this hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Bradenton Beach and Coquina Beach are located ...
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
101 22nd St Bradenton Beach FL
3.19 km from city center
Stay at this hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
6900 Gulf Dr Holmes Beach FL
1.39 km from city center
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3 out of 5
2218 Gulf Drive N Bradenton Beach FL
2.99 km from city center
Book a stay at this beach apartment in Bradenton Beach. Enjoy free WiFi, free parking, and a private beach. Popular attractions Bradenton Beach and Coquina Beach ...
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
202 1st St N Bradenton Beach FL
4.56 km from city center
Stay at this apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. ...
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
6306 Gulf Dr Holmes Beach FL
1.01 km from city center
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our ...
Silver Surf Gulf Beach Resort

Silver Surf Gulf Beach Resort

3 out of 5
1301 Gulf Dr N Bradenton Beach FL
3.74 km from city center
Book a stay at this beach hotel in Bradenton Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
2200 Gulf Dr N Bradenton Beach FL
3.11 km from city center
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 ...
Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
8102 Gulf Drive Holmes Beach FL
2.18 km from city center
Stay at this apartment in Holmes Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
5108 Gulf Dr Holmes Beach FL
0.18 km from city center
Stay at this motel in Holmes Beach. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Bradenton Beach and Anna Maria Beach are located ...
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
2710 Gulf Drive N Holmes Beach FL
2.25 km from city center
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 ...
Waterline Villas & Marina, Autograph Collection

Waterline Villas & Marina, Autograph Collection

4 out of 5
5325 Marina Drive Holmes Beach FL
0.31 km from city center
Book a stay at this business-friendly hotel in Holmes Beach. Enjoy free WiFi, a marina, and room service. Popular attractions Bradenton Beach and Anna Maria ...
Bridgewalk Resort

Bridgewalk Resort

3.5 out of 5
100 Bridge Street Bradenton Beach FL
4.61 km from city center
Stay at this aparthotel in Bradenton Beach. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
Via Roma Beach Resort

Via Roma Beach Resort

4 out of 5
2408 Gulf Dr N Bradenton Beach FL
2.74 km from city center
Book a stay at this beach aparthotel in Bradenton Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bradenton Beach and Coquina Beach ...
Alamanda Villas

Alamanda Villas

3.5 out of 5
102 39th St Holmes Beach FL
0.89 km from city center
Book a stay at this beach condo in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bradenton Beach and Anna Maria Beach ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Jan 11 - Thu, Jan 28
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$305 Roundtrip, found 2 days ago
$305
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Jan 11 from Detroit Metropolitan Wayne County to Sarasota-Bradenton Intl., returning Thu, Jan 28, priced at $305 found 2 days ago
United
Tue, Dec 1 - Sat, Dec 5
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Select United flight, departing Tue, Dec 1 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Sat, Dec 5, priced at $349 found 5 days ago
Delta
Mon, Jan 11 - Thu, Jan 28
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$358 Roundtrip, found 2 days ago
$358
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jan 11 from Detroit Metropolitan Wayne County to Sarasota-Bradenton Intl., returning Thu, Jan 28, priced at $358 found 2 days ago
American Airlines
Mon, Jan 11 - Mon, Jan 18
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$369 Roundtrip, found 5 days ago
$369
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Jan 11 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Mon, Jan 18, priced at $369 found 5 days ago
JetBlue Airways
Mon, Nov 16 - Fri, Nov 20
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Nov 16 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Fri, Nov 20, priced at $412 found 1 day ago