Anna Maria Island Vacation Rentals

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Vacation Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (307)
"Great location"
$204 nightly
The price is $231
Oct 27 - Oct 28
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Bridgewalk Resort
3.5 star property
9.2 out of 10, Wonderful, (752)
"Great location and staff were knowledgeable about surrounding areas.. "
$284 nightly
The price is $321
Oct 15 - Oct 16
Total with taxes and fees
Bridgewalk Resort
Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (42)
"Awesome place to stay "
$276 nightly
The price is $312
Oct 15 - Oct 16
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
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! "
$210 nightly
The price is $237
Oct 19 - Oct 20
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
9.4 out of 10, Exceptional, (41)
"Great location, great people, awsome hosts, very prompt and caring. "
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
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
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
10.0 out of 10, Exceptional, (1)
"What a beautiful home! Location was perfect, linens towels, decoration was on point! My husband had a blast with the putting green. Loved it!"
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
3.0 star property
9.6 out of 10, Exceptional, (14)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
Private Pool & Hot Tub - House close to Beach and Bridge Street
10.0 out of 10, Exceptional, (3)
"Wonderful property that is comfortably close to beach. Everything at the property was what we needed and the downstairs area was super nice. This really is a hidden gem next to cortez beach. "
Private Pool & Hot Tub - House close to Beach and Bridge Street
Anna Maria Sunsets - studio
9.0 out of 10, Wonderful, (223)
" Very clean great location and property owner very nice and understanding thank you for everything "
$217 nightly
The price is $242
Oct 15 - Oct 16
Total with taxes and fees
Anna Maria Sunsets - studio
Anna Maria Island -walk to the beach!
9.8 out of 10, Exceptional, (14)
"Nice space for our stay "
Anna Maria Island -walk to the beach!
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
9.8 out of 10, Exceptional, (288)
"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. "
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, (238)
"Enjoyed the pool & comfort & cleanliness of our studio. Our stay was fantastic. We enjoyed walking to local restaurants & enjoyed music played at various restaurants. Would highly recommend the studio for a great time on the beach & fun in the sun. "
$257 nightly
The price is $286
Oct 20 - Oct 21
Total with taxes and fees
Anna Maria Sunsets - studio
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
2.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful stay ! Our family loved it ! "
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
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
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
10.0 out of 10, Exceptional, (184)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
9.8 out of 10, Exceptional, (121)
"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
Cozy Cottage
9.6 out of 10, Exceptional, (24)
"Wonderful little place for the little getaway my daughter and I needed"
Cozy Cottage
Anna Maria Island - 2/1
9.6 out of 10, Exceptional, (175)
"Great location a great weekend getaway"
$284 nightly
The price is $316
Oct 20 - Oct 21
Total with taxes and fees
Anna Maria Island - 2/1
Beachfront HUGE TWO FLOOR UNIT-Sunset Balconies/Walk to all Restaurants/Shops!!!
9.6 out of 10, Exceptional, (29)
"Andrew is a wonderful host and we trust him to provide us with thr best stay. He always does."
$789 nightly
The price is $880
Oct 21 - Oct 22
Total with taxes and fees
Beachfront HUGE TWO FLOOR UNIT-Sunset Balconies/Walk to all Restaurants/Shops!!!
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

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 $231 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.