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.
Hampton Inn Odessa Trinity

Hampton Inn Odessa Trinity

2.5 out of 5
Trinity
Price was $669, price is now $527 per person
$527
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Odessa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old McMicky's Farm and Crescent Lake are located nearby.

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $934, price is now $637 per person
$637
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Landing Apartments near Sun City Center and Riverview

Landing Apartments near Sun City Center and Riverview

4 out of 5
Save 100% on your flight
Price was $1,210, price is now $900 per person
$900
per person
Jun 18 - Jun 26
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Wimauma. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Lake Wimauma and Sandpiper Golf Club are located nearby.

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $708, price is now $542 per person
$542
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Price was $759, price is now $593 per person
$593
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Stay at this hotel in Sarasota. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Hyatt House Tampa Downtown

Hyatt House Tampa Downtown

3.5 out of 5
Downtown Tampa
Price was $882, price is now $698 per person
$698
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa are located nearby.

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Top Hotel Deals

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 ...
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 ...
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 ...
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 ...
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 Bradenton Beach and Coquina Beach ...
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
2.24 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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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See all available properties in Anna Maria Island
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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.

Delta
Tue, Sep 22 - Tue, Sep 29
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 22 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Sep 29, priced at $237 found 5 days ago
Southwest Airlines
Wed, May 27 - Tue, Jun 2
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, May 27 from Midway Intl. to Sarasota-Bradenton Intl., returning Tue, Jun 2, priced at $237 found 3 days ago
JetBlue Airways
Tue, Jul 21 - Thu, Jul 30
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 7 hours ago
$237
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Tue, Jul 21 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Thu, Jul 30, priced at $237 found 7 hours ago
American Airlines
Tue, Jun 9 - Wed, Jun 10
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 9 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Wed, Jun 10, priced at $250 found 1 day ago
United
Sat, May 9 - Fri, May 15
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$252 Roundtrip, found 2 days ago
$252
Roundtrip
found 2 days ago
Select United flight, departing Sat, May 9 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Fri, May 15, priced at $252 found 2 days ago