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.
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Tampa Heights Bungalow - Bed & Breakfast

Tampa Heights Bungalow - Bed & Breakfast

3 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Hotel South Tampa & Suites

Hotel South Tampa & Suites

2.5 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Hilton Garden Inn Tampa Airport Westshore

Hilton Garden Inn Tampa Airport Westshore

3 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Extended Stay America Premier Suites Tampa Fairgrounds Casin

Extended Stay America Premier Suites Tampa Fairgrounds Casin

2.5 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
La Quinta Inn by Wyndham Clearwater Central

La Quinta Inn by Wyndham Clearwater Central

3 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Holiday Inn Express & Suites Tampa East - Ybor City by IHG

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

2.5 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Extended Stay America Suites - Tampa - Casino Area

Extended Stay America Suites - Tampa - Casino Area

2.5 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
The Westin Tampa Waterside

The Westin Tampa Waterside

4 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)

4-night Anna Maria Island vacations

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

ZenHomes

3 out of 5
per person
Jun 18 - Jun 22
found 2 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Ramada by Wyndham Temple Terrace/Tampa North

Ramada by Wyndham Temple Terrace/Tampa North

2.5 out of 5
per person
Jun 18 - Jun 22
found 2 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 22
found 2 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Tampa (TPA)
Comfort Inn Sun City Center - Ruskin - Tampa South

Comfort Inn Sun City Center - Ruskin - Tampa South

2.5 out of 5
per person
Jun 18 - Jun 22
found 2 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 6
found 10 hours ago
Roundtrip flight included
Kansas City (MCI) to Sarasota (SRQ)
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Jun 10 - Jun 14
found 23 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Tampa (TPA)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 6
found 10 hours ago
Roundtrip flight included
Kansas City (MCI) to Sarasota (SRQ)
The Ringling Beach House

The Ringling Beach House

3.5 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 6
found 10 hours ago
Roundtrip flight included
Kansas City (MCI) to Sarasota (SRQ)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Jun 2 - Jun 6
found 10 hours ago
Roundtrip flight included
Kansas City (MCI) to Tampa (TPA)
Carlisle Inn

Carlisle Inn

3.5 out of 5
per person
May 29 - Jun 2
found 3 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
May 29 - Jun 2
found 3 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Carlisle Inn

Carlisle Inn

3.5 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
per person
Jun 16 - Jun 21
found 12 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Sarasota (SRQ)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Sarasota (SRQ)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
per person
May 26 - May 31
found 7 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.

Thu, Jul 10 - Sun, Jul 13
EWR
New York
SRQ
Sarasota
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jul 10 from New York to Sarasota, returning Sun, Jul 13, priced at $177 found 3 days ago
Wed, May 14 - Wed, May 21
JFK
New York
SRQ
Sarasota
$189 Roundtrip, found 14 hours ago
$189
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, May 14 from New York to Sarasota, returning Wed, May 21, priced at $189 found 14 hours ago
Sat, Apr 26 - Wed, Apr 30
PHL
Philadelphia
SRQ
Sarasota
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 26 from Philadelphia to Sarasota, returning Wed, Apr 30, priced at $217 found 6 days ago

Top rated hotels for your Anna Maria Island vacation

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
6306 Gulf Dr, Holmes Beach, FL
0.62 mi from city center
The price is $700 per night
$700
includes taxes & fees
$620 per night
Apr 27 - Apr 28
When you stay at Anna Maria Beach Resort in Holmes Beach, you'll be on the beach, within a 10-minute drive of Anna Maria Beach and Bean Point Beach.
Pool
Hot Tub
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 $618 per night
$618
includes taxes & fees
$547 per night
May 19 - May 20
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 Bean Point Beach and Anna Maria Beach.
Pool
Spa
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
202 1st St N, Bradenton Beach, FL
2.83 mi from city center
The price is $372 per night
$372
includes taxes & fees
$329 per night
May 7 - May 8
When you stay at Pelican Post at Anna Maria Island Inn in Bradenton Beach, you'll be in the entertainment district, within a 5-minute drive of Cortez Beach and Coquina Beach.
Pool
Hot Tub
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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.