Cheap Vacations in Anna Maria Island

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3-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $415, price is now $259 per person
$259
per person
May 3 - May 6
found 1 day ago
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
Price was $1,285, price is now $843 per person
$843
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $635, price is now $431 per person
$431
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $855, price is now $587 per person
$587
per person
May 7 - May 10
found 21 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
Price was $821, price is now $564 per person
$564
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $852, price is now $602 per person
$602
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Sarasota (SRQ)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $780, price is now $556 per person
$556
per person
May 3 - May 6
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Save 100% on your flight
Price was $3,757, price is now $2,749 per person
$2,749
per person
Apr 20 - Apr 23
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
Price was $807, price is now $596 per person
$596
per person
May 5 - May 8
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $752, price is now $556 per person
$556
per person
May 3 - May 6
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,347, price is now $1,004 per person
$1,004
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $1,577, price is now $1,178 per person
$1,178
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)

4-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $658, price is now $406 per person
$406
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Price was $682, price is now $453 per person
$453
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $652, price is now $434 per person
$434
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Price was $827, price is now $557 per person
$557
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sarasota (SRQ)
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
Save 100% on your flight
Price was $821, price is now $559 per person
$559
per person
Apr 26 - Apr 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
Save 100% on your flight
Price was $978, price is now $669 per person
$669
per person
May 1 - May 5
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $1,533, price is now $1,069 per person
$1,069
per person
May 3 - May 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Price was $1,135, price is now $796 per person
$796
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,864, price is now $1,320 per person
$1,320
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $822, price is now $587 per person
$587
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,300, price is now $932 per person
$932
per person
Apr 16 - Apr 20
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $568, price is now $408 per person
$408
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)

5-night Anna Maria Island vacations

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $795, price is now $485 per person
$485
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,289, price is now $837 per person
$837
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,430, price is now $934 per person
$934
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $966, price is now $641 per person
$641
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
The Fold Hotels Indian Shores

The Fold Hotels Indian Shores

3 out of 5
Price was $1,154, price is now $767 per person
$767
per person
Apr 14 - Apr 19
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
Price was $876, price is now $595 per person
$595
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,346, price is now $917 per person
$917
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,278, price is now $882 per person
$882
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,051, price is now $752 per person
$752
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $2,671, price is now $1,934 per person
$1,934
per person
Apr 27 - May 2
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
The Avalon Club

The Avalon Club

4 out of 5
Price was $1,952, price is now $1,417 per person
$1,417
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $852, price is now $620 per person
$620
per person
Apr 15 - Apr 20
found 1 day 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.
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
Save 100% on your flight
Price was $855, price is now $588 per person
$588
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,729, price is now $1,506 per person
$1,506
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,526, price is now $929 per person
$929
per person
Apr 23 - Apr 30
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,451, price is now $884 per person
$884
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,655, price is now $1,061 per person
$1,061
per person
May 2 - May 9
found 1 day ago
Roundtrip 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
Price was $1,136, price is now $738 per person
$738
per person
Apr 24 - Apr 30
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,041, price is now $708 per person
$708
per person
Apr 24 - Apr 30
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,229, price is now $842 per person
$842
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,361, price is now $932 per person
$932
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
Save 100% on your flight
Price was $2,378, price is now $1,646 per person
$1,646
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Save 100% on your flight
Price was $1,416, price is now $983 per person
$983
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

4 out of 5
Save 100% on your flight
Price was $1,832, price is now $1,297 per person
$1,297
per person
Apr 15 - Apr 21
found 19 hours ago
Roundtrip flight included
New York (NYC) 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.

Thu, Apr 9 - Tue, Apr 14
ATL
Atlanta
SRQ
Sarasota
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Atlanta to Sarasota, returning Tue, Apr 14, priced at $193 found 1 day ago
Sun, Apr 5 - Thu, Apr 9
BOS
Boston
SRQ
Sarasota
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Apr 5 from Boston to Sarasota, returning Thu, Apr 9, priced at $197 found 6 days ago
Mon, Jul 20 - Mon, Jul 27
EWR
New York
SRQ
Sarasota
$227 Roundtrip, found 6 days ago
$227
Roundtrip
found 6 days ago
Select United flight, departing Mon, Jul 20 from New York to Sarasota, returning Mon, Jul 27, priced at $227 found 6 days ago

Top rated hotels for your Anna Maria Island vacation

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
$473 nightly
The price is $535 total per night
$535 total
Apr 12 - Apr 13
Total with taxes and fees
When you stay at Bali Hai Beachfront Resort and Spa in Holmes Beach, you'll be on the waterfront, a 1-minute drive from Bradenton Beach and 5 minutes from Bean Point Beach.
On private beach
Pool
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.5 out of 5
202 1st St N Bradenton Beach FL
2.83 mi from city center
$303 nightly
The price is $342 total per night
$342 total
Apr 12 - Apr 13
Total with taxes and fees
With a stay at Pelican Post at Anna Maria Island Inn in Bradenton Beach, you'll be in the entertainment district, a 3-minute walk from Bradenton Beach and a 4-minute drive from Coquina Beach.
Pool
Hot Tub
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3 out of 5
2218 Gulf Drive N Bradenton Beach FL
1.86 mi from city center
$324 nightly
The price is $366 total per night
$366 total
Apr 13 - Apr 14
Total with taxes and fees
When you stay at Seabreeze at Anna Maria Island Inn in Bradenton Beach, you'll be on the beach, a 1-minute drive from Bradenton Beach and 5 minutes from Coquina Beach.
Pet friendly
Parking included
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.