Anna Maria Island Vacation Rentals

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Vacation Rentals in Anna Maria Island

Our top choices for Anna Maria Island vacation rentals

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (298)
"Place was very clean and perfect location for the beach/surrounding restaurants."
$223 nightly
The price is $252
Sep 1 - Sep 2
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (33)
"Awesome place to stay "
$246 nightly
The price is $278
Sep 3 - Sep 4
Total with taxes and fees
Seabreeze at Anna Maria Island Inn

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (738)
"Very nice rooms and location "
$273 nightly
The price is $309
Sep 9 - Sep 10
Total with taxes and fees
Bridgewalk Resort

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (382)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (60)
"Perfect home for a family getaway "
$497 nightly
The price is $554
Sep 3 - Sep 4
Total with taxes and fees
Adorable Beach cottage just steps Bean Point beach!

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

9.4 out of 10, Exceptional, (3)
"Well maintained propert and enjoyed our stay."
$1,190 nightly
The price is $1,330
Sep 7 - Sep 8
Total with taxes and fees
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (119)
"Such a beautiful property! We can't wait to go back!"
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Villas By The Sea #2, Anna Maria Island Condo, one block from beach, heated pool

10.0 out of 10, Exceptional, (98)
"We had a wonderful stay and our host was very informative and helpful. I would definitely stay here again "
Villas By The Sea #2, Anna Maria Island Condo, one block from beach, heated pool

Anna Maria Sunsets - studio

9.0 out of 10, Wonderful, (218)
" Very clean great location and property owner very nice and understanding thank you for everything "
$203 nightly
The price is $226
Sep 3 - Sep 4
Total with taxes and fees
Anna Maria Sunsets - studio

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

9.4 out of 10, Exceptional, (38)
"Great home with all needed comforts. Beach is right behind it when is low tide, otherwise beach access is only a block away. Home is clean, modern and comfortable with amazing sunrises. "
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (170)
"Property worked great for our family "
$285 nightly
The price is $317
Sep 1 - Sep 2
Total with taxes and fees
Anna Maria Island - 2/1

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (277)
"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (233)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
$214 nightly
The price is $238
Aug 31 - Sep 1
Total with taxes and fees
Anna Maria Sunsets - studio

Beachfront - New Listing!

10.0 out of 10, Exceptional, (26)
"The Diamond Star has it all! The kitchen is fully stocked, and they provide everything you need for a day at the beach. There are tons of games for family! The house is immaculate, and the location is fantastic! We were able to walk to get ice cream, dinner, and breakfast effortlessly. Our family loved the pool and watching the sunsets from the decks! Nicole was a wonderful host, going above and beyond to ensure we had everything we needed! "
Beachfront - New Listing!

Beachfront Home | Pool + Spa | Games | Ocean Views

10.0 out of 10, Exceptional, (38)
"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"
Beachfront Home | Pool + Spa | Games | Ocean Views

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

$1,177 nightly
The price is $1,311
Sep 1 - Sep 2
Total with taxes and fees
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

Sunset View Pet Friendly w/Pool Beach Home

2.0 star property
10.0 out of 10, Exceptional, (20)
"This house was perfection! I want to stay here every single year!"
$630 nightly
The price is $705
Sep 1 - Sep 2
Total with taxes and fees
Sunset View Pet Friendly w/Pool Beach Home

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

3.0 star property
9.4 out of 10, Exceptional, (12)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (184)
"Great location. Private beach with great sun rise view. Close to local shops and restaurants "
$676 nightly
The price is $754
Sep 17 - Sep 18
Total with taxes and fees
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10.0 out of 10, Exceptional, (181)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
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.
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Top Anna Maria Island Hotel Reviews

Find out more about Anna Maria Island

Find out more about Anna Maria Island

Everything you need to know about Anna Maria Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Anna Maria Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $226 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.