Anna Maria Vacation Rentals from ￥73,342: Search Short-Term Rentals

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Our top choices for Anna Maria vacation rentals

1. Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Anna Maria

Kyle K.

￥75,516 total

includes taxes & fees

Sep 14 - Sep 15

2. Beautiful Bungalow with Pool and Bay Views!

Anna Maria

Silvia

￥97,323 total

includes taxes & fees

Aug 18 - Aug 19

3. Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria

courtneyharned

￥73,342 total

includes taxes & fees

Sep 14 - Sep 15

4. Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Anna Maria

Daniela S.

￥93,160 total

includes taxes & fees

Aug 27 - Aug 28

5. Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria

Christina R.

￥79,190 total

includes taxes & fees

Sep 14 - Sep 15

6. Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Anna Maria

Stacey D.

￥79,190 total

includes taxes & fees

Sep 14 - Sep 15

7. Tiny Tides: Adorable Cozy House!

Anna Maria

karen l.

￥84,138 total

includes taxes & fees

Aug 19 - Aug 20

8. Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

Anna Maria

J I.

￥76,265 total

includes taxes & fees

Sep 14 - Sep 15

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Top Anna Maria Hotel Reviews

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

10/10 Excellent

"The location is even better than the pictures. Absolutely gorgeous!"

The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem

10/10 Excellent

"The place was great!I am going to list the things I wish I had known about first..It is a main road for everyone and their mother to come to the beach. People constantly being dropped off and picked up, Turing around in the driveway, lots of foot traffic and everything.Bring your own beach chairs and equipment. The chairs there are terrible and in awful condition.The pool table is very small, and is not level, so it’s really not usable, also there was no chalk.You don’t have direct access to the beach from the property, you have to walk down the driveway and use the public access, which I think most of the houses are like that there.Bring all of your toiletries, the soap they give you is no bueno. I think the worst part was there was no blackout shade in the master bedroom so it was VERY bright in the morning, this is probably the sole reason why I wouldn’t ever rent this house again. Besides the negative, it was great being next to the beach, the house was clean and very cool. It’s sole purpose is rental VRBO so don’t expect anything luxurious, furniture, mattresses glassware, rugs, are all cheap and made to be thrown away. We had a great time but I don’t think I would go back to Anna Maria, I’d probably stay in Longboat or something next time, you literally can’t go anywhere at 5:00 or near dinner time without waiting in traffic for 30mins. Anyways, pretty much exactly what I expected it to be."

Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything

10/10 Excellent

"Place was great. Nice to have a private pool. Only issue we did not know about is that the master bedroom there is no door separating the toilet/tub. And the master bedroom the bed is smaller than the other bedroom. But it worked out fine.We also did not realize there was a shed in between the two rentals that had beach, chairs, wagon, inflatables, etc.,until the second day, but I probably just missed it on the listing."

Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!

10/10 Excellent

"Extremely clean cute house. It had everything we could have thought of that we may need. From beach gear, cleaning supplies and anything in between. Loved this place and made our stay very enjoyable!"

Newly Renovated w/Heated Pool/Spa/Bistro, Stunning Views, Minutes from the Beach

8/10 Good

"Clean and great communication with host. Only thing I wish we had known prior was the downstairs condo was not as updated/nice as the upstairs one and although the patio furniture is super nice- they all have cushions so with all the rain there wasn’t much patio furniture to utilize on the deck(which over looks the ocean-that was awesome) a few small polywood type table/chairs on the upper deck would have been so nice for evening games, etc. overall, a GREAT location and hosts were very kind and responsive. Both units were clean and had many “extras” (like coolers, beach blanket, chairs, life jackets, bikes etc.). Pool area was also very nice and clean. Our family had a wonderful time staying here!"

Find out more about Anna Maria

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Frequently asked questions

Can I find a vacation rental in Anna Maria?

Yes, we give you a choice of vacation rentals close to top points of interest in Anna Maria, or you can go with a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Anna Maria. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best vacation rentals that Anna Maria has to offer?

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!: Visitors give good reviews to this Anna Maria vacation home rental, which is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Anna Maria are ANNA MARIA GEM- adorable 3BR/2BA NEWLY REDONE HOUSE -JUST STEPS FROM THE BEACH and Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything.

How many vacation rentals are there in Anna Maria?

With 590 Expedia vacation rentals, you're sure to find just the right place for your Anna Maria stay.

What can I see and do in Anna Maria?

Cultural attractions include Anna Maria Island Museum and Historical Park and Island Players, whereas Anna Maria Beach and Bean Point Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places like Lido Beach and Tampa Bay.

What are vacation rentals like in Anna Maria?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Anna Maria. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips.

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Check prices for these dates

Our top choices for Anna Maria vacation rentals

1. Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

2. Beautiful Bungalow with Pool and Bay Views!

3. Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

4. Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

5. Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

6. Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

7. Tiny Tides: Adorable Cozy House!

8. Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

9. Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

10. Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

11. Dog friendly cottage - One block to the Bay!

12. Emerald Shores East! Walk to Beach!

13. Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

14. Beachside Duplex w/ Pool and Private Suite

15. Beautiful Guest House Near the Beach with Private Pool!

16. Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

17. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

18. Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl

19. Remodeled Duplex with Heated Pool, 2 Blocks to the Beach!

20. Adorable Cottage with Covered Balconies and Private Pool

Find vacation rentals that suit your style

Top Anna Maria Hotel Reviews

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Ideal Location, Stunning Villa! Close to beach, beach gear provided!

The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem

Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything

North End Duplex with Pool on Anna Maria Island! Near Bean Point

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

Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Newly Renovated w/Heated Pool/Spa/Bistro, Stunning Views, Minutes from the Beach

Find out more about Anna Maria

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