Anna Maria Island Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Anna Maria Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $894, price is now $596 per person
$596
per person
May 6 - May 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 St. Armands Circle and Lido Beach are located nearby.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,690, price is now $1,002 per person
$1,002
per person
May 3 - May 10
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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.
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,556, price is now $953 per person
$953
per person
May 30 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) 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.
Mar Bay Motel &Suites
Save 100% on your flight
Price was $1,098, price is now $720 per person
$720
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions BayCare Ballpark and Philippe Park are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,144, price is now $770 per person
$770
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 St. Armands Circle and Lido Beach are located nearby.
The Avalon Club
Save 100% on your flight
Price was $2,927, price is now $2,017 per person
$2,017
per person
May 3 - May 10
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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.
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See all available trips from Columbus to Anna Maria Island
View all tripsTop Hotel Deals
Bali Hai Beachfront Resort and Spa
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
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
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 ...
Tortuga Inn Beach Resort
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 ...
Haley's at The Anna Maria Island Inn
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 ...
Anna Maria Beach Resort
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 ...
The Retreat at Anna Maria Island Inn
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 ...
Driftwood at Anna Maria Island Inn
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 ...
Seaside at Anna Maria Island Inn
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 ...
Cedar Cove Resort and Cottages
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 ...
Bridgewalk Resort
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 ...
Silver Surf Gulf Beach Resort
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 ...
Tradewinds Beach Resort
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 propertiesLowest 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.
Sat, Apr 18 - Mon, May 4
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$194 Roundtrip, found 8 hours ago
$194
Roundtrip
found 8 hours ago
Tue, Apr 28 - Tue, May 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$247 Roundtrip, found 8 hours ago
$247
Roundtrip
found 8 hours ago
Wed, Apr 29 - Mon, May 4
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Wed, Apr 22 - Wed, Apr 29
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$247 Roundtrip, found 6 days ago
$247
Roundtrip
found 6 days ago
Mon, Apr 27 - Thu, Apr 30
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago