A marina with boats, a bridge, and high-rise buildings.

Anna Maria Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Anna Maria vacation rentals

A beach with clear turquoise water and white sand.

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

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Anna Maria
10.0 out of 10, Exceptional, (29 reviews)
"Cottage 107 was ver clean, comfortable, and had everything we needed. The property was quiet and very family friendly. The beach, just a very short half block walk, is gorgeous. We had a wonderful time!"
United States
Terry R.
$561 nightly
The price is $629
Oct 3 - Oct 4
Total with taxes and fees
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
A modern living room with a grey sofa, a striped armchair, a coffee table, and a bookshelf.

2. Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Anna Maria
9.8 out of 10, Exceptional, (208 reviews)
"We absolutely loved this house and will be back again! The decoration is very cute and the home has many details that you notice that lots of love has been put into it. Literally 1 block from the beach, the location is perfect! They have bikes and beach gear available which was a plus. Beds were very comfortable; the kitchen had everything you need, even coffee pods! We also loved the pool and surroundings."
United States
Carolina
$657 nightly
The price is $737
Sep 28 - Sep 29
Total with taxes and fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
A wooden boardwalk surrounded by dense foliage.

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

Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
Anna Maria
9.2 out of 10, Wonderful, (14 reviews)
"Close walk to the beach "
United States
Zev C.
$492 nightly
The price is $552
Sep 28 - Sep 29
Total with taxes and fees
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
A beach with clear turquoise water and white sand.

4. Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
10.0 out of 10, Exceptional, (23 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
$562 nightly
The price is $630
Oct 3 - Oct 4
Total with taxes and fees
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A living room with a television, a sofa, a chair, and a view of a river.

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

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
$494 nightly
The price is $554
Sep 28 - Sep 29
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A tropical garden with a stone pathway, bamboo fence, and a staircase leading to a wooden deck.

6. Beach Don't Kill My Vibe by Beach Boutique Rentals

Beach Don't Kill My Vibe by Beach Boutique Rentals
Anna Maria
10.0 out of 10, Exceptional, (22 reviews)
"Great location, accurate description and photos, host was very welcoming."
United States
Justin W.
$459 nightly
The price is $515
Sep 29 - Sep 30
Total with taxes and fees
Beach Don't Kill My Vibe by Beach Boutique Rentals
A spacious living area with a high ceiling, a dining table with chairs, a gray sofa, a television, and a staircase leading to an upper level.

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

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Anna Maria
9.8 out of 10, Exceptional, (73 reviews)
"Everything was clean, great location right near the beach, the kids loved everything and the pool was amazing! Wish the propane tanks got replaced before we checked in as we would have loved to use the grill."
United States
Emily I.
$722 nightly
The price is $809
Sep 29 - Sep 30
Total with taxes and fees
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
A beach with clear turquoise water and white sand.

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

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (33 reviews)
"Great place to stay!Nice walk to the beach!"
United States
Rose Y.
$407 nightly
The price is $457
Sep 28 - Sep 29
Total with taxes and fees
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
A beachfront property with a two-story house, a sandy beach, and several Adirondack chairs.

9. SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
9.6 out of 10, Exceptional, (215 reviews)
"It was great!"
United States
Megan
$622 nightly
The price is $698
Oct 4 - Oct 5
Total with taxes and fees
SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
A wooden deck with a table and chairs overlooking a calm body of water, a dock with a boat, and a clear sky.

10. Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
ANNA MARIA
9.6 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay. Great location, and beautiful water view. Would defiantly stay again"
United States
Tina H.
$557 nightly
The price is $625
Sep 28 - Sep 29
Total with taxes and fees
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
A beach with gentle waves and a sunset.

11. 2nd House from the Beach with No Roads to Cross

2nd House from the Beach with No Roads to Cross
Anna Maria
10.0 out of 10, Exceptional, (180 reviews)
"Overall a perfect house for the price and the location was perfect to the beach. All the extra beach gear was great."
United States
Jason V.
2nd House from the Beach with No Roads to Cross
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

12. Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
Anna Maria
9.8 out of 10, Exceptional, (20 reviews)
"Great house! Great host!"
United States
Katie K.
$1,284 nightly
The price is $1,439
Sep 28 - Sep 29
Total with taxes and fees
Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
A bedroom with a large bed, a potted plant, and a TV.

13. Coconut Cottage~Private Heated Pool~Block to shops

Coconut Cottage~Private Heated Pool~Block to shops
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our family of four. We love the north end of the island and it was within walking distance of the beach and local shops. The house was clean and the host responds very well. We would stay here again!"
United States
Jenny R.
$778 nightly
The price is $873
Sep 28 - Sep 29
Total with taxes and fees
Coconut Cottage~Private Heated Pool~Block to shops
A modern living room with a blue sofa, a TV, and a kitchen area with a white countertop and bar stools.

14. Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
Anna Maria
9.6 out of 10, Exceptional, (45 reviews)
"My husband and I had a great week staying here. We had everything that we needed for our stay, the house was very comfortable. We loved spending time in the pool and spa!"
United States
Jesse Z.
$728 nightly
The price is $817
Sep 28 - Sep 29
Total with taxes and fees
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
A beach with clear turquoise water and white sand.

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

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Anna Maria
10.0 out of 10, Exceptional, (42 reviews)
"Loved the easy access to the beach and the fact that the property had beach supplies available for you to use. We had great service when needed and will definitely visit again !"
United States
Meagan
$399 nightly
The price is $448
Sep 30 - Oct 1
Total with taxes and fees
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
A beach with clear turquoise water and white sand.

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

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Anna Maria
9.4 out of 10, Exceptional, (30 reviews)
"Old Florida charm of cottage. Beautiful location and only steps to the beach. Staff was wonderful and room was clean."
United States
Christina R.
$418 nightly
The price is $469
Sep 28 - Sep 29
Total with taxes and fees
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
A poolside area with lounge chairs and umbrellas, surrounded by palm trees and a wooden fence.

17. Kiwi Cottage~Private Heated Pool!~Shopping close!

Kiwi Cottage~Private Heated Pool!~Shopping close!
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Perfect location! Walking distance to beaches, shops and restaurants! The pool was an added bonus"
United States
Christopher
$661 nightly
The price is $742
Sep 28 - Sep 29
Total with taxes and fees
Kiwi Cottage~Private Heated Pool!~Shopping close!
A spacious kitchen with a large island, stainless steel appliances, and a chandelier.

18. Pine Avenue next door!~Heated pool~Steps to Beach

Pine Avenue next door!~Heated pool~Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Nice size rooms. Pool was in the shade but very clean. All around a great stay"
United States
Kelly F.
$1,021 nightly
The price is $1,146
Sep 28 - Sep 29
Total with taxes and fees
Pine Avenue next door!~Heated pool~Steps to Beach
A covered outdoor area with wooden flooring, white railings, and a ceiling fan.

19. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
$775 nightly
The price is $870
Oct 25 - Oct 26
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
A beach with gentle waves and a sunset.

20. Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (163 reviews)
"We really enjoyed this location - steps away from the beach was awesome. Also walking distance from some of our favorite spots (Waterfront, Donut Experiment, North Shore, Poppo’s, Two Scoops). We will be booking this spot on our next trip to Anna Maria."
United States
Zachary Z.
$490 nightly
The price is $550
Sep 30 - Oct 1
Total with taxes and fees
Do you love the beach?
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 Hotel Reviews

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

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

10/10 Excellent
"Loved this place- would stay again. Really made it a great trip!"
Gavin H. 4-night trip
Posted 1 day ago
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Price trends for vacation rentals in Anna Maria

Less expensive
More expensive
Next month
September
March
$588
Month
Price
January
$648
February
$861
March
$887
April
$725
May
$551
June
$691
July
$777
August
$571
September
$540
October
$588
November
$561
December
$708
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Anna Maria. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Anna Maria

Everything you need to know about Anna Maria 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 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria. 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 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 $698 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 rentals

At Expedia, we put the best Anna Maria 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Perfect Anna Maria. Dock on Canal - 3 blocks to sugar sand beach. Heated pool. and Coral Cove: Walk to the Beach! Heated pool! Prime North End!.

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.