Anna Maria Island Holiday Rentals

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Holiday Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (301)
"Place was very clean and perfect location for the beach/surrounding restaurants."
Pelican Post at Anna Maria Island Inn

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (747)
"Great location and staff were knowledgeable about surrounding areas.. "
The price is AU$442
includes taxes & fees
12 Oct - 13 Oct
Bridgewalk Resort

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (38)
"Awesome place to stay "
Seabreeze at Anna Maria Island Inn

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

9.4 out of 10, Exceptional, (40)
"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!

Beachfront - New Listing!

10.0 out of 10, Exceptional, (26)
"We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!"
Beachfront - New Listing!

Anna Maria Sunsets - studio

9.0 out of 10, Wonderful, (221)
" Very clean great location and property owner very nice and understanding thank you for everything "
The price is AU$394
includes taxes & fees
29 Sept - 30 Sept
Anna Maria Sunsets - studio

POOL and New Spa!! Private outdoor living with grill, tv, and refrigerator.

9.8 out of 10, Exceptional, (287)
"Great spot! Loved the pool and spa, and the outdoor area with the grill, TV, and fridge made it super easy to hang out and relax. Nice private setup—just a few small details could be improved, but overall a really good stay. "
POOL and New Spa!! Private outdoor living with grill, tv, and refrigerator.

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (383)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort

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

9.0 out of 10, Wonderful, (4)
"Well maintained propert and enjoyed our stay."
The price is AU$2,426
includes taxes & fees
28 Sept - 29 Sept
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

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

10.0 out of 10, Exceptional, (1)
"The house is beautiful!! Plenty of room for a family, and plenty to do!The owner was readily available through messages and the phone if we had any questions. It was an easy process, and an excellent experience!!!I highly recommend this house if you just feel like hanging out, or exploring Anna Maria, it’s a beautiful location!!And don’t forget to go down the slide!! "
The price is AU$2,274
includes taxes & fees
20 Oct - 21 Oct
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

Beachfront HUGE TWO FLOOR UNIT-Sunset Balconies/Walk to all Restaurants/Shops!!!

9.6 out of 10, Exceptional, (27)
"Very nice location to stay. Only issue we had was parking was very tight so prepare for that if you have a large suv or truck. "
The price is AU$1,030
includes taxes & fees
12 Oct - 13 Oct
Beachfront HUGE TWO FLOOR UNIT-Sunset Balconies/Walk to all Restaurants/Shops!!!

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (172)
"Super cute condo so close to the beach "
The price is AU$451
includes taxes & fees
28 Sept - 29 Sept
Anna Maria Island - 2/1

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (236)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
The price is AU$470
includes taxes & fees
28 Sept - 29 Sept
Anna Maria Sunsets - studio

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

9.8 out of 10, Exceptional, (62)
"Perfect home for a family getaway "
The price is AU$654
includes taxes & fees
1 Oct - 2 Oct
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

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

9.8 out of 10, Exceptional, (120)
"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

Haley's at The Anna Maria Island Inn

3.0 star property
8.6 out of 10, Excellent, (375)
"The staff members were so nice and super helpful!! Place was so cute! "
Haley's at The Anna Maria Island Inn

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

3.0 star property
9.4 out of 10, Exceptional, (13)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Bay Front Condo - Anna Maria Island Sunsets

9.8 out of 10, Exceptional, (19)
"We loved this condo. It was so clean and perfect for our family."
The price is AU$700
includes taxes & fees
3 Oct - 4 Oct
Bay Front Condo - Anna Maria Island Sunsets

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

9.6 out of 10, Exceptional, (186)
"Bay view was nice "
The price is AU$1,150
includes taxes & fees
27 Oct - 28 Oct
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!

9.8 out of 10, Exceptional, (12)
"We loved our time here and can’t wait to book it for next year!"
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!
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$394 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.