Cheap Vacations in Anna Maria Island

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Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Highland Down Town Tampa

Highland Down Town Tampa

3.5 out of 5
Old Seminole Heights
Save 100% on your flight
per person
Dec 23 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hampton Inn Tampa Downtown Channel District

Hampton Inn Tampa Downtown Channel District

3 out of 5
Downtown Tampa
Save 100% on your flight
per person
Dec 23 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Siesta Key Palms Resort

Siesta Key Palms Resort

4 out of 5
per person
Dec 23 - Dec 26
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Hemingway

The Hemingway

4 out of 5
per person
Dec 25 - Dec 28
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

3.5 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

3.5 out of 5
per person
Dec 23 - Dec 27
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Jan 16 - Jan 20
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

3.5 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Dec 24 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
The Saint Hotel

The Saint Hotel

2 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hilton St. Petersburg Carillon Park

Hilton St. Petersburg Carillon Park

3.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Highland Down Town Tampa

Highland Down Town Tampa

3.5 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)
Hampton Inn Tampa Downtown Channel District

Hampton Inn Tampa Downtown Channel District

3 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 29
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jan 11 - Jan 18
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Silver Sands

Silver Sands

3.5 out of 5
Save 100% on your flight
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Sarasota (SRQ)

Flight deals to Anna Maria Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Feb 2 - Fri, Feb 7
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 2 from Philadelphia to Sarasota, returning Fri, Feb 7, priced at $68 found 1 day ago
Fri, Feb 7 - Mon, Feb 10
ORD
Chicago
SRQ
Sarasota
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Feb 7 from Chicago to Sarasota, returning Mon, Feb 10, priced at $126 found 2 days ago
Mon, Feb 10 - Tue, Feb 18
BOS
Boston
SRQ
Sarasota
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Mon, Feb 10 from Boston to Sarasota, returning Tue, Feb 18, priced at $137 found 17 hours ago

Top rated hotels for your Anna Maria Island vacation

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
6900 Gulf Dr, Holmes Beach, FL
0.87 mi from city center
The price is $421 per night
$421
includes taxes & fees
$376 per night
Dec 10 - Dec 11
With a stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, within a 15-minute drive of Coquina Beach and Bradenton Beach.
Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

2.5 out of 5
1325 Gulf Drive North, Bradenton Beach, FL
2.28 mi from city center
Get rates
When you stay at Tortuga Inn Beach Resort in Bradenton Beach, you'll be near the beach, within a 15-minute drive of Coquina Beach and IMG Academy.
Luxury home with Pool, Putting Green, Beach Bikes!

Luxury home with Pool, Putting Green, Beach Bikes!

1.91 mi from city center
Get rates
With a stay at this vacation home in Bradenton Beach, you'll be by the sea, within a 10-minute drive of Coquina Beach and Anna Maria Sound.
Don't see what you're looking for?
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.