Cheap Vacations in Anna Maria Island

Choose two or more items and save on your trip:

Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
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
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jan 20 - Jan 23
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
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
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota, an IHG Hotel

voco Sarasota, an IHG Hotel

3.5 out of 5
Central Sarasota
Save 100% on your flight
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Suite Dreams Guesthouse aka Care Takeover Home

Suite Dreams Guesthouse aka Care Takeover Home

3.5 out of 5
Save 100% on your flight
per person
Feb 4 - Feb 9
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)

3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
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
Jan 24 - Jan 27
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Jan 20 - Jan 23
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
The Wayland Condos By Barsala

The Wayland Condos By Barsala

4 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

4 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 26
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
voco Sarasota, an IHG Hotel

voco Sarasota, an IHG Hotel

3.5 out of 5
per person
Feb 14 - Feb 17
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
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
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
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
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Wayland Condos By Barsala

The Wayland Condos By Barsala

4 out of 5
Save 100% on your flight
per person
Jan 24 - Jan 28
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
voco Sarasota, an IHG Hotel

voco Sarasota, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
Feb 14 - Feb 18
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Turtle Beach Resort and Inn

Turtle Beach Resort and Inn

3.5 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Legacy Vacation Resorts - Indian Shores

Legacy Vacation Resorts - Indian Shores

3 out of 5
Save 100% on your flight
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
New York (JFK) 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
Jan 31 - Feb 5
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

4 out of 5
Save 100% on your flight
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
The Wayland Condos By Barsala

The Wayland Condos By Barsala

4 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop 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
Feb 13 - Feb 18
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Turtle Beach Resort and Inn

Turtle Beach Resort and Inn

3.5 out of 5
Save 100% on your flight
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Barsala At The Wayland Apartments

Barsala At The Wayland Apartments

4 out of 5
Save 100% on your flight
per person
Jan 31 - Feb 5
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

6-7 night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
ZenHomes in Tampa near Busch Gardens

ZenHomes in Tampa near Busch Gardens

3 out of 5
per person
Feb 11 - Feb 17
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
per person
Feb 5 - Feb 12
found 1 day ago
Roundtrip flight included
New York (NYC) 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
Feb 5 - Feb 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
The Gemma by Brightwild

The Gemma by Brightwild

4.5 out of 5
Save 100% on your flight
per person
Jan 25 - Feb 1
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

3.5 out of 5
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
New York (NYC) 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
Feb 5 - Feb 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flight
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Crown House 4b Pool Home 6 Mins to IR Beach

The Crown House 4b Pool Home 6 Mins to IR Beach

2 out of 5
Save 100% on your flight
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Bardmoor a Luxury Family Retreat in St Pete

The Bardmoor a Luxury Family Retreat in St Pete

2 out of 5
Save 100% on your flight
per person
Jan 25 - Feb 1
found 14 hours ago
Roundtrip flight included
Chicago (ORD) 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 19 - Fri, Jan 24
PHL
Philadelphia
SRQ
Sarasota
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jan 19 from Philadelphia to Sarasota, returning Fri, Jan 24, priced at $68 found 2 days ago
Wed, Mar 19 - Wed, Mar 26
ORD
Chicago
SRQ
Sarasota
$68 Roundtrip, found 23 hours ago
$68
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, Mar 19 from Chicago to Sarasota, returning Wed, Mar 26, priced at $68 found 23 hours ago
Thu, Jan 30 - Sun, Feb 2
LGA
New York
SRQ
Sarasota
$153 Roundtrip, found 5 days ago
$153
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Jan 30 from New York to Sarasota, returning Sun, Feb 2, priced at $153 found 5 days 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
Get rates
With a stay at Silver Surf Gulf Beach Resort in Bradenton Beach, you'll be by the ocean, within a 15-minute drive of IMG Academy and Anna Maria Sound.
Pool
Breakfast included
Luxury home with Pool, Putting Green, Beach Bikes!

Luxury home with Pool, Putting Green, Beach Bikes!

1.91 mi from city center
Get rates
Located in Bradenton Beach, this vacation home is by the sea, within a 5-minute walk of Anna Maria Sound and Aluna Wellness Center & Spa.
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 $398 per night
$398
includes taxes & fees
$352 per night
Jan 20 - Jan 21, 2025
With a stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the beach, just steps from Bradenton Beach and a 2-minute drive from Island Gallery West.
Pool
Spa
Don't see what you're looking for?
See all available properties in Anna Maria Island
View all properties
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.