Anna Maria Island Holiday Rentals

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Holiday Rentals in Anna Maria Island

Our top choices for Anna Maria Island holiday 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."
The price is AU$387
includes taxes & fees
1 Sept - 2 Sept
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 "
The price is AU$478
includes taxes & fees
1 Sept - 2 Sept
Seabreeze at Anna Maria Island Inn

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (738)
"Very nice rooms and location "
The price is AU$448
includes taxes & fees
9 Sept - 10 Sept
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 "
The price is AU$856
includes taxes & fees
3 Sept - 4 Sept
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."
The price is AU$2,054
includes taxes & fees
7 Sept - 8 Sept
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 "
The price is AU$350
includes taxes & fees
9 Sept - 10 Sept
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 "
The price is AU$491
includes taxes & fees
9 Sept - 10 Sept
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."
The price is AU$369
includes taxes & fees
3 Sept - 4 Sept
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

The price is AU$2,030
includes taxes & fees
1 Sept - 2 Sept
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!"
The price is AU$1,112
includes taxes & fees
1 Sept - 2 Sept
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 "
The price is AU$1,166
includes taxes & fees
17 Sept - 18 Sept
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Anna Maria Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria Island holiday rentals we have selected for you start as low as AU$350 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island holiday 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 holiday.

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.