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.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Port Tampa City
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul 9 - Jul 11
Roundtrip flight included
Philadelphia (PHL) 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
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jun 16 - Jun 19
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 11
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Westshore
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 21 - Jun 23
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 14 - Jun 17
Roundtrip flight included
Philadelphia (PHL) 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
Jul 9 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 19
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Sirata Beach Resort

Sirata Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar

3 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 18
Roundtrip non-stop flight included
Chicago (ORD) to Sarasota (SRQ)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 1 - Jul 5
Roundtrip flight included
Philadelphia (PHL) 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
Jul 1 - Jul 5
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Trenton (TTN) 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
Jul 3 - Jul 7
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Trenton (TTN) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Bellwether Beach Resort

Bellwether Beach Resort

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Trenton (TTN) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 7
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Capri at Siesta

The Capri at Siesta

3 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 2
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 2
Roundtrip flight included
Philadelphia (PHL) to Sarasota (SRQ)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
The Avalon Club

The Avalon Club

4 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) 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
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

2.5 out of 5
per person
Jun 20 - Jun 25
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Howard Johnson by Wyndham Clearwater / Dunedin

Howard Johnson by Wyndham Clearwater / Dunedin

2 out of 5
per person
Jun 20 - Jun 25
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham Clearwater South

La Quinta Inn & Suites by Wyndham Clearwater South

2.5 out of 5
per person
Jun 20 - Jun 25
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
La Quinta Inn by Wyndham Tampa Bay Pinellas Park Clearwater

La Quinta Inn by Wyndham Tampa Bay Pinellas Park Clearwater

2.5 out of 5
per person
Jun 20 - Jun 25
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

3 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

3 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Sonesta Simply Suites Clearwater

Sonesta Simply Suites Clearwater

2 out of 5
per person
Jun 20 - Jun 25
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Sheraton Sand Key Resort

Sheraton Sand Key Resort

4 out of 5
per person
Jun 30 - Jul 5
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

La Quinta Inn & Suites by Wyndham USF (Near Busch Gardens)

2.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham Tampa Brandon Regency Park

La Quinta Inn & Suites by Wyndham Tampa Brandon Regency Park

2.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
La Quinta Inn by Wyndham Tampa Near Busch Gardens

La Quinta Inn by Wyndham Tampa Near Busch Gardens

2.5 out of 5
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
La Quinta Inn & Suites by Wyndham Tampa Central

La Quinta Inn & Suites by Wyndham Tampa Central

2.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Hampton Inn & Suites Tampa Northwest/Oldsmar

Hampton Inn & Suites Tampa Northwest/Oldsmar

2.5 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Residence Inn by Marriott Tampa Westshore/Airport

Residence Inn by Marriott Tampa Westshore/Airport

3 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 29
Roundtrip non-stop flight included
Indianapolis (IND) 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, Jul 28 - Thu, Aug 15
PHL
Philadelphia
SRQ
Sarasota
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jul 28 from Philadelphia to Sarasota, returning Thu, Aug 15, priced at $88 found 5 days ago
Tue, Aug 27 - Wed, Sep 11
JFK
New York
SRQ
Sarasota
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 27 from New York to Sarasota, returning Wed, Sep 11, priced at $147 found 1 day ago
Thu, May 30 - Sat, Jun 15
ORD
Chicago
SRQ
Sarasota
$155 Roundtrip, found 9 hours ago
$155
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, May 30 from Chicago to Sarasota, returning Sat, Jun 15, priced at $155 found 9 hours ago

Top rated hotels for your Anna Maria Island vacation

Silver Surf Gulf Beach Resort

Silver Surf Gulf Beach Resort

3 out of 5
1301 Gulf Dr N, Bradenton Beach, FL
2.32 mi from city center
The price is $231 per night
$231
per night
May 29 - May 30
When you stay at Silver Surf Gulf Beach Resort in Bradenton Beach, you'll be by the ocean, within a 15-minute drive of Coquina Beach and Anna Maria Beach.
Perfectly Located Home with Pool and Spa

Perfectly Located Home with Pool and Spa

1.91 mi from city center
Get rates
When you stay at this vacation home in Bradenton Beach, you'll be by the sea, within a 15-minute drive of Coquina Beach and Anna Maria Beach.
Pool
Pet friendly
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 $374 per night
$374
per night
May 14 - May 15
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, within a 10-minute drive of Anna Maria Beach and Bean Point Beach.
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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.

^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.