Anna Maria Island Vacation Packages for 2025
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.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $672, price is now $455 per person
$455
per person
Dec 5 - Dec 10
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. 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.
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
Save 100% on your flight
Price was $958, price is now $589 per person
$589
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 4-star business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.
Ramada by Wyndham Tampa Westshore Airport South
Westshore
Save 100% on your flight
Price was $735, price is now $457 per person
$457
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,179, price is now $761 per person
$761
per person
Dec 5 - Dec 11
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 4-star 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.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
Save 100% on your flight
Price was $691, price is now $484 per person
$484
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.
Hotel Alba, Tapestry Collection by Hilton
Westshore
Save 100% on your flight
Price was $1,008, price is now $728 per person
$728
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk 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
Stay at this 3.5-star beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean ...
Pelican Post at Anna Maria Island Inn
202 1st St N, Bradenton Beach, FL
4.56 km from city center
Stay at this 3-star apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in ...
Anna Maria Beach Resort
6306 Gulf Dr, Holmes Beach, FL
1.01 km from city center
Stay at this 3.5-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Haley's at The Anna Maria Island Inn
8102 Gulf Drive, Holmes Beach, FL
2.18 km from city center
Stay at this 3-star apartment in Holmes Beach. Enjoy free WiFi, free parking, and daily housekeeping. 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 3.5-star aparthotel in Bradenton Beach. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Seabreeze at Anna Maria Island Inn
2218 Gulf Drive N, Bradenton Beach, FL
2.99 km from city center
Stay at this 3-star beach apartment in Bradenton Beach. Enjoy free WiFi, free parking, and a private beach. Popular attractions Coquina Beach and Bean Point ...
Cedar Cove Resort and Cottages
2710 Gulf Drive N, Holmes Beach, FL
2.24 km from city center
Stay at this 3-star beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition ...
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 Coquina Beach and Bean Point Beach are located ...
Silver Surf Gulf Beach Resort
1301 Gulf Dr N, Bradenton Beach, FL
3.74 km from city center
Stay at this 3-star beach hotel in Bradenton Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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 ...
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 Bean ...
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 Anna Maria Beach and Bean Point Beach are located ...
Waterline Villas & Marina, Autograph Collection
5325 Marina Drive, Holmes Beach, FL
0.31 km from city center
Stay at this 4-star business-friendly hotel in Holmes Beach. Enjoy free WiFi, a marina, and room service. Popular attractions Anna Maria Beach and Bean Point ...
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, Nov 15 - Tue, Nov 18
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Wed, Nov 12 - Thu, Nov 13
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Wed, Nov 12 - Thu, Nov 13
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Wed, Jan 7 - Sun, Jan 11
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago