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.
Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
Price was $556, price is now $427 per person
$427
per person
Dec 13 - Dec 20
found 12 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,686, price is now $1,008 per person
$1,008
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $702, price is now $490 per person
$490
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was $1,278, price is now $893 per person
$893
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Save 100% on your flight
Price was $899, price is now $655 per person
$655
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,018, price is now $746 per person
$746
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,156 per person
$1,156
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
Peninsula Bed & Cocktails

Peninsula Bed & Cocktails

4 out of 5
Price was $772, price is now $583 per person
$583
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Price was $718, price is now $549 per person
$549
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Hemingway

The Hemingway

4 out of 5
Rocky Point
Price was $739, price is now $570 per person
$570
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
Price was $423, price is now $330 per person
$330
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,229, price is now $854 per person
$854
per person
Dec 3 - Dec 6
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $702, price is now $490 per person
$490
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,067, price is now $810 per person
$810
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Shoreline Island Resort - Exclusively Adult

Shoreline Island Resort - Exclusively Adult

3 out of 5
Price was $488, price is now $373 per person
$373
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $552, price is now $427 per person
$427
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $800, price is now $619 per person
$619
per person
Nov 27 - Nov 30
found 9 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $622, price is now $489 per person
$489
per person
Nov 27 - Nov 30
found 9 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $1,015, price is now $807 per person
$807
per person
Dec 3 - Dec 6
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Little Harbor

Little Harbor

2 out of 5
Price was $490, price is now $393 per person
$393
per person
Dec 10 - Dec 13
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Price was $506, price is now $406 per person
$406
per person
Dec 20 - Dec 23
found 6 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $791, price is now $636 per person
$636
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $630, price is now $487 per person
$487
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,229, price is now $858 per person
$858
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was $762, price is now $547 per person
$547
per person
Dec 20 - Dec 24
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Shoreline Island Resort - Exclusively Adult

Shoreline Island Resort - Exclusively Adult

3 out of 5
Price was $760, price is now $558 per person
$558
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $767, price is now $564 per person
$564
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,330, price is now $978 per person
$978
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $951, price is now $711 per person
$711
per person
Nov 29 - Dec 3
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $869, price is now $650 per person
$650
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,156 per person
$1,156
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Price was $718, price is now $549 per person
$549
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Southern PAG Beach House Bungalows

Southern PAG Beach House Bungalows

3 out of 5
Price was $1,510, price is now $1,167 per person
$1,167
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Price was $1,488, price is now $1,158 per person
$1,158
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Price was $784, price is now $605 per person
$605
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,255, price is now $819 per person
$819
per person
Dec 1 - Dec 6
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,109, price is now $758 per person
$758
per person
Dec 17 - Dec 22
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was $884, price is now $605 per person
$605
per person
Nov 29 - Dec 4
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Price was $1,018, price is now $707 per person
$707
per person
Dec 12 - Dec 17
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $1,278, price is now $893 per person
$893
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop 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
Price was $1,575, price is now $1,135 per person
$1,135
per person
Dec 15 - Dec 20
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,141, price is now $829 per person
$829
per person
Dec 15 - Dec 20
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,434, price is now $1,047 per person
$1,047
per person
Dec 17 - Dec 22
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Price was $840, price is now $620 per person
$620
per person
Dec 12 - Dec 17
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $968, price is now $722 per person
$722
per person
Dec 17 - Dec 22
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $834, price is now $638 per person
$638
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
Price was $556, price is now $427 per person
$427
per person
Dec 13 - Dec 20
found 12 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Price was $1,077, price is now $754 per person
$754
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
BAY INN

BAY INN

2 out of 5
Price was $879, price is now $644 per person
$644
per person
Dec 13 - Dec 20
found 12 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,686, price is now $1,008 per person
$1,008
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
CW Resort

CW Resort

4 out of 5
Price was $1,108, price is now $696 per person
$696
per person
Dec 11 - Dec 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,492, price is now $979 per person
$979
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,478, price is now $987 per person
$987
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $2,403, price is now $1,646 per person
$1,646
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $908, price is now $623 per person
$623
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,378, price is now $952 per person
$952
per person
Dec 11 - Dec 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $940, price is now $653 per person
$653
per person
Dec 11 - Dec 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,151, price is now $803 per person
$803
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)

Flight deals to Anna Maria Island

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

Sun, Jan 24 - Thu, Jan 28
TTN
Trenton
PIE
St. Petersburg
$78 Roundtrip, found 18 hours ago
$78
Roundtrip
found 18 hours ago
Select Allegiant Air flight, departing Sun, Jan 24 from Trenton to St. Petersburg, returning Thu, Jan 28, priced at $78 found 18 hours ago
Fri, Nov 13 - Mon, Nov 16
PHL
Philadelphia
PIE
St. Petersburg
$121 Roundtrip, found 4 days ago
$121
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Fri, Nov 13 from Philadelphia to St. Petersburg, returning Mon, Nov 16, priced at $121 found 4 days ago
Mon, Feb 1 - Fri, Feb 5
BOS
Boston
SRQ
Sarasota
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Mon, Feb 1 from Boston to Sarasota, returning Fri, Feb 5, priced at $130 found 3 days ago

Top rated hotels for your Anna Maria Island vacation

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
1.83 mi from city center
$146 nightly
The price is $165 total per night
$165 total
Oct 28 - Oct 29
Total with taxes and fees
When you stay at The Retreat at Anna Maria Island Inn in Bradenton Beach, you'll be near the beach, a 3-minute drive from Bradenton Beach and 6 minutes from Coquina Beach.
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
101 22nd St Bradenton Beach FL
Free Cancellation
Reserve now, pay when you stay
1.98 mi from city center
$183 nightly
The price is $207 total per night
$207 total
Oct 29 - Oct 30
Total with taxes and fees
When you stay at Tropic Isle at Anna Maria Island Inn in Bradenton Beach, you'll be by the ocean, a 1-minute drive from Bradenton Beach and 5 minutes from Coquina Beach.
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

4 out of 5
6900 Gulf Dr Holmes Beach FL
0.86 mi from city center
$272 nightly
The price is $307 total per night
$307 total
Nov 18 - Nov 19
Total with taxes and fees
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, a 1-minute drive from Bradenton Beach and 5 minutes from Bean Point Beach.
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.

Top Picks

^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.