Anna Maria Island Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

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 ...
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 Coquina Beach and Anna Maria Beach are located ...
Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

2.5 out of 5
1325 Gulf Drive North Bradenton Beach FL
3.67 km from city center
Book a stay at this beach hotel in Bradenton Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
2710 Gulf Drive N Holmes Beach FL
2.24 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 ...
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 ...
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. ...
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 Anna Maria 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 Anna Maria Beach and Bradenton Beach are located ...
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 Anna Maria Beach and ...
Captain's Quarters at Anna Maria Island Inn

Captain's Quarters at Anna Maria Island Inn

3.5 out of 5
110-112 8th St Bradenton Beach FL
5.05 km from city center
Book a stay at this beach motel in Bradenton Beach. Enjoy free parking, a private beach, and daily housekeeping. Popular attractions Anna Maria Beach and Coquina ...
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 ...
Tradewinds Beach Resort

Tradewinds Beach Resort

2.5 out of 5
1603 Gulf Drive North Bradenton Beach FL
3.57 km from city center
Stay at this condo in Bradenton Beach. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
Don't see what you're looking for?
See all available properties in Anna Maria Island
View all properties
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.

JetBlue Airways
Fri, Jul 10 - Mon, Jul 27
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Jul 10 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Jul 27, priced at $197 found 5 days ago
American Airlines
Fri, Jul 17 - Fri, Jul 24
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jul 17 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Jul 24, priced at $207 found 5 days ago
Delta
Wed, Jul 29 - Wed, Aug 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 29 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 5, priced at $217 found 4 days ago
Southwest Airlines
Wed, Jul 29 - Wed, Aug 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jul 29 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 5, priced at $217 found 4 days ago
United
Fri, Jul 10 - Mon, Jul 27
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$244 Roundtrip, found 5 days ago
$244
Roundtrip
found 5 days ago
Select United flight, departing Fri, Jul 10 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Jul 27, priced at $244 found 5 days ago