Anna Maria Island Vacations from $800

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Your Anna Maria Island Vacation

Secure a vacation package to Anna Maria Island and enjoy travel on your own terms. You'll be charmed by its watersports, coastal beaches and fishing. Get your trip to Anna Maria Island off to a flying start by exploring its best cities. Bradenton Beach is one you cannot miss. Whether you're planning to travel for a few days or a few weeks, Expedia are here to help you organize your next dream Anna Maria Island vacation.

The Latest Anna Maria Island vacation packages

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

Innisbrook Resort

Save 100% on your flight
$800
per person
Jan 9 - Jan 16
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,004 reviews)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$1,129
per person
Dec 7 - Dec 14
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
Beautiful old florida style resort Beautiful rooms comfortable beds right on the powdery white sand beach and turquoise water

Reviewed on Oct 18, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
$1,093
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
Clean room I like

Reviewed on Oct 18, 2026

La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille
Save 100% on your flight
$1,055
per person
Jan 5 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (36 reviews)
Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!! The property is so beautiful and well cared for that I’d hate to see someone destroy something!

Reviewed on Oct 18, 2026

Captiva Beach Resort

Captiva Beach Resort

South Village
Save 100% on your flight
$862
per person
Jan 9 - Jan 16
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,312 reviews)
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Where to stay in Anna Maria Island

Find the best Anna Maria Island areas and neighborhoods for the activities you enjoy most. Learn more about Anna Maria Island
An aerial view of a beach with numerous umbrellas and people, a clear blue ocean, and a cityscape in the background.

Ilexhurst

If you're spending some time in Ilexhurst, Anna Maria Sound and Bradenton Beach are top sights worth seeing.

A wooden pier extending into a body of water with a clear blue sky above.

Bridge Street

1 out of top 10 points of interest in this area

While visiting Bridge Street, you might make a stop by sights like Bradenton Beach and Bridge Street.

A beach with sand dunes and tall grasses at sunset.

Key Royale

While Key Royale might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bradenton Beach and Holmes Beach Beaches.

Stay near popular Anna Maria Island attractions

A sunset over a grassy field with a path leading to the water.

Bean Point Beach

10.0/10 (1 review)
If a restful vacation is part of your travel plans, Bean Point Beach might be the perfect place to seek out during your trip to Anna Maria. Take in the museums and sunsets in the area.
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A coastal beach with clear turquoise waters, a sandy shore, and a line of trees along the beachfront.

Coquina Beach

9.4/10 (818 reviews)
Coquina Beach dazzles with pristine white sands and turquoise waters on Anna Maria Island's southern tip. Enjoy swimming and dolphin-watching under the shade of Australian pine trees.
See properties
A sandy beach with people sunbathing and swimming, a clear blue sky, and buildings in the background.

Cortez Beach

9.6/10 (307 reviews)
Cortez Beach enchants with its pristine white sands and turquoise Gulf waters on Anna Maria Island. Enjoy uninterrupted sunsets and natural shoreline far from commercial developments.
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A waterfront scene with a clock tower, palm trees, and a pier extending into the water.

Historic Bridge Street Pier

9.6/10 (356 reviews)
This historic pier, once the gateway to Anna Maria Island, is now a vibrant community hub. Stroll the waterfront, fish from the deck, or savor fresh seafood while enjoying panoramic bay views.
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Anna Maria Beach

9.6/10 (72 reviews)
Why not spend a lazy afternoon at Anna Maria Beach during your trip to Anna Maria? Stroll along the beaches or discover the area's sunrises.
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Holmes Beach Beaches

10.0/10 (1 review)
Why not spend a lazy afternoon at Holmes Beach Beaches during your trip to Holmes Beach? While you're in the area, stroll along the beautiful beaches.
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What to do in Anna Maria Island

Manatee Discovery Anna Maria Island

Manatee Discovery Anna Maria Island

$55
per adult
Manatee Discovery Anna Maria Island
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

$109
per adult
100% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
The Island Tour

The Island Tour

$65
per adult
The Island Tour
See all activities in Anna Maria Island

Anna Maria Island Hotel Deals

The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

2305 Gulf Dr N Bradenton Beach FL
$161 nightly
$182 total
Nov 16 - Nov 17
Total with taxes and fees
The Retreat at Anna Maria Island Inn
Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

6900 Gulf Dr Holmes Beach FL
$214 nightly
$242 total
Nov 18 - Nov 19
Total with taxes and fees
8.6/10 Excellent! (782 reviews)
"Excellent location. Professional staff. Clean and comfy rooms."

Reviewed on Oct 16, 2026

Bali Hai Beachfront Resort and Spa
Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

101 22nd St Bradenton Beach FL
Fully refundableReserve now, pay when you stay
$158 nightly
$179 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (739 reviews)
"Very cute hotel but rooms were not really clean. The floors were disgusting."

Reviewed on Oct 18, 2026

Tropic Isle at Anna Maria Island Inn
See all 3,855 properties in Anna Maria Island
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.

Find the Best Anna Maria Island Vacation Packages

Things to do near Anna Maria Island

Anna Maria Island is perfect for beach and outdoor family vacations, offering a variety of activities. Enjoy stunning beach vacations, take a day trip to explore the area, play tennis at local courts, or visit nearby theme parks. For a unique experience, don't miss the hour-long dolphin cruise to see these playful creatures up close. With options for relaxation and recreation, Anna Maria Island is an ideal getaway for everyone.

Shopping

Visit West Coast Surf Shop, just 0.6 miles from Anna Maria Island, for surf gear and beachwear. Explore Bridge Street, 3 miles away, for a charming shopping area with a mix of local businesses. For a larger selection, check out Ellenton Premium Outlets, 13 miles from the island.

Recreation

At Aluna Wellness Center & Spa, indulge in rejuvenating treatments that promote relaxation and well-being, just 2 miles from the island. For family fun, visit Fish Hole Adventure Golf, a lively mini-golf venue offering sports and adventure vibes, located 3 miles away.

Adventure

Experience the thrill of paddleboarding with AMI Paddleboard Adventures, located 0.6 miles from Anna Maria Island. Dive into underwater exploration with Blue Water Explorers, situated 3 miles away. For family fun, visit the Astro Skate and Fun Center, found 10 miles from the island.

Nightlife

Experience the laid-back nightlife of Anna Maria Island with a visit to The Sandbar, where you can enjoy beachfront dining and live music. For a more casual vibe, check out the Island Pub for great drinks and friendly locals, perfect for unwinding after a day in the sun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Anna Maria Island

Anna Maria Island is a perfect destination for beach and outdoor family vacations, offering attractions like pristine beaches, historical museums, and cultural experiences. Visitors can enjoy the beautiful Anna Maria Beach and explore local points of interest that highlight the island's charm. Whether you're seeking relaxation or adventure, Anna Maria Island provides a delightful mix of activities for every traveler looking for the best beach getaway.

  • Anna Maria Beach: Experience the quintessential beach vibes at Anna Maria Beach, located a short 3 miles from Anna Maria Island. With its soft white sands and gentle waves, it's perfect for sunbathing, swimming, and enjoying picturesque sunsets.
  • Bean Point Beach: Just 3 miles from Anna Maria Island, Bean Point Beach offers stunning scenery and a tranquil atmosphere. This cape is ideal for beachcombing, picnicking, and taking in breathtaking views of the Gulf of Mexico.
  • IMG Academy: Situated 8 miles from Anna Maria Island, IMG Academy is a premier sports training facility. While it's more focused on sports education, visitors can appreciate the impressive campus and various athletic events held throughout the year.

Best time to go to Anna Maria Island

The best time to visit Anna Maria Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.4°F (16.900000000000002°C)Light RainMostly SunnyAverageAverage
February64.8°F (18.2°C)No RainMostly SunnyAverageSlightly High
March67.8°F (19.9°C)No RainMostly SunnyModerately HighSlightly High
April73.0°F (22.8°C)Light RainSunnyAverageSlightly High
May77.5°F (25.3°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyModerately HighAverage
July83.1°F (28.4°C)Light RainMostly SunnyModerately HighAverage
August83.7°F (28.700000000000003°C)Light RainMostly SunnyAverageAverage
September81.7°F (27.6°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately LowSlightly Low
December66.4°F (19.1°C)Light RainMostly SunnyModerately LowAverage

Tips to save on your trip to Anna Maria Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Anna Maria Island during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Anna Maria Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tampa Intl. Airport (TPA)

More vacations you might like

Frequently asked questions

How do vacation package prices compare across popular destinations in Anna Maria Island?
For an Anna Maria Island vacation package, Bradenton Beach typically offers lower prices for a week-long trip compared to Holmes Beach.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Anna Maria Island vacation package?
When you bundle, you can save up to 30%*. To save money on a Anna Maria Island package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in an Anna Maria Island vacation package?
An Anna Maria Island vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like Holmes Beach or Bradenton Beach.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
Which destinations in Anna Maria Island offer the best-value vacation package deals?
Holmes Beach and Bradenton Beach are some of the top destinations for cheap Anna Maria Island vacation package deals. For an affordable weekend getaway, Holmes Beach is often among the most budget-friendly options, with package prices starting around $760 per adult. For notable bundle savings, Holmes Beach is also a strong option, with flight-and-hotel bundles saving around $180 per adult.Browse cheap vacation packages in Anna Maria Island on Expedia to compare current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
When is the best time to visit the top destinations in Anna Maria Island?
The best time for an Anna Maria Island vacation package depends on which destination you choose.Holmes Beach sees its peak booking months in April, August, and September. April offers average temperatures around 73°F, while September is warmer with averages around 82°F. If you'd prefer fewer crowds, May and December are quieter, with average highs around 78°F and 66°F respectively.Bradenton Beach is most popular from July to August, and in December. July is warm with average temperatures around 83°F, and December is cooler with averages around 66°F. For a quieter trip, February and November are good choices, with average highs around 65°F and 70°F.
What package types are available across the top destinations in Anna Maria Island?
Anna Maria Island vacation packages offer diverse travel styles, primarily centered around the popular areas of Holmes Beach and Bradenton Beach:
  • Budget: In Bradenton Beach, Silver Surf Gulf Beach Resort, rated 9.4 out of 10 by travelers, provides amenities like free breakfast and kitchenettes, with travelers often praising the excellent staff and great breakfast.
  • Beach: For beach-focused trips, Anna Maria Beach Resort in Holmes Beach, a 3.5-star property rated 9.2 out of 10 by travelers, features a hot tub and outdoor pool, and travelers frequently highlight the amazing views and spacious rooms.
  • Family: Holmes Beach offers family-friendly options like Cedar Cove Resort and Cottages, rated 9.1 out of 10 by travelers, which includes family rooms and a game room, and travelers often find the overall atmosphere cozy and the rooms big.
  • Couples: In Holmes Beach, Bali Hai Beachfront Resort and Spa, a 4-star property rated 8.9 out of 10 by travelers, is well-suited for couples with its bar/lounge, spa, and outdoor pool, and travelers frequently praise its perfect location and lovely overall ambiance.
  • Pet-friendly: Bradenton Beach features pet-friendly stays such as Tropic Isle at Anna Maria Island Inn, a 4-star property rated 9 out of 10 by travelers, offering an outdoor pool and pet-friendly accommodations, with travelers often praising the excellent overall experience and the staff.
Which destinations should I consider for an Anna Maria Island vacation?
For an Anna Maria Island vacation, pick your base by the kind of trip you want:
  • Holmes Beach: A well-established package base, ideal for families and those seeking abundant outdoor activities and scenic beach views.
  • Bradenton Beach: Another popular package base, offering a mix of beach relaxation, family-friendly attractions, and some urban amenities.
  • Anna Maria: A good lodging base known for its tranquil atmosphere, scenic views, and outdoor activities, perfect for a more relaxed beach getaway.
Is Anna Maria Island better suited for a beach vacation or a cultural trip?
An Anna Maria Island vacation is primarily suited for a beach vacation, given its reputation for beautiful white sand beaches and abundant outdoor activities. Each of its constituent towns, including Holmes Beach, Bradenton Beach, and Anna Maria, is known for its scenic coastal views and family-friendly attractions.There are some cultural elements to explore. You can visit the Anna Maria Island Historical Society to learn about the island's past or catch a performance at the Island Players theater. Overall, travelers seeking sun, sand, and sea will find Anna Maria Island an ideal destination, with cultural sights offering a pleasant diversion.
Which airports serve the main destinations in Anna Maria Island?
For an Anna Maria Island vacation, several airports provide convenient access to the region. Tampa International Airport (TPA) serves the Tampa Bay area, while Southwest Florida International Airport (RSW) is located near Fort Myers. Sarasota-Bradenton International Airport (SRQ) is the closest option, serving Sarasota and Bradenton, which is one of Anna Maria Island's constituent cities. Your choice will depend on your specific travel plans and preferred airline.
What are the top things to do across the destinations in Anna Maria Island?
An Anna Maria Island vacation offers a variety of activities across its distinct towns and areas:Browse and book things to do in Anna Maria Island on Expedia.
Are there family vacation packages in Anna Maria Island with kid-friendly amenities?
Family vacation packages in Anna Maria Island can feature accommodations with kid-friendly amenities, particularly in areas like Holmes Beach:
  • Cedar Cove Resort and Cottages: In Holmes Beach, this resort, rated 9.1 out of 10 by travelers, offers family rooms, a game room, and a kitchen, making it a comfortable base for families. Travelers often find the overall atmosphere cozy and the rooms big.
When should I book vacation packages for the top destinations in Anna Maria Island?
Booking times for an Anna Maria Island vacation package vary by destination, with most travelers booking around 6 to 7 weeks before departure.Travelers tend to book trips to these destinations most often in April, from July to September, and in December. If you're planning a spontaneous getaway, Expedia also offers last-minute Anna Maria Island vacation packages.
How many days do you need for an Anna Maria Island vacation?
Most Anna Maria Island vacation packages last around 4 days, but the ideal trip length depends on where you're going and what you'd like to experience.Holmes Beach, primarily known for its beaches and outdoor activities, is well-suited for a trip of around 4 days. Both weekend and week-long stays are popular, allowing time to enjoy the sands of Manatee Public Beach.Bradenton Beach, also a beach-focused destination with outdoor activities, is ideal for a stay of around 4 days. Travelers often choose weekend or week-long trips to explore areas like Cortez Beach and its surroundings.
Can I change or cancel my Anna Maria Island vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Anna Maria Island vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Anna Maria Island vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Anna Maria Island vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Anna Maria Island?
To find last-minute vacation packages to Anna Maria Island, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Anna Maria Island vacation packages?
Free cancellation on a Anna Maria Island vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Anna Maria Island vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Anna Maria Island getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Anna Maria Island vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.