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

Anna Maria Vacation Rentals

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Our top choices for Anna Maria vacation rentals

1. 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, (205 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
$720 nightly
The price is $802
Aug 30 - Aug 31
Total with taxes and fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

2. 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, (21 reviews)
"Great location, accurate description and photos, host was very welcoming."
United States
Justin W.
$479 nightly
The price is $533
Aug 26 - Aug 27
Total with taxes and fees
Beach Don't Kill My Vibe by Beach Boutique Rentals

3. AUG, SEPT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

AUG, SEPT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
9.6 out of 10, Exceptional, (212 reviews)
"It was great!"
United States
Megan
$726 nightly
The price is $808
Aug 25 - Aug 26
Total with taxes and fees
AUG, SEPT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

4. 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.
$587 nightly
The price is $654
Aug 25 - Aug 26
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

5. 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.
$789 nightly
The price is $879
Aug 25 - Aug 26
Total with taxes and fees
Coconut Cottage~Private Heated Pool~Block to shops

6. Family-Friendly Canal Retreat with Pool and Steps to the Beach

Family-Friendly Canal Retreat with Pool and Steps to the Beach
Anna Maria
9.8 out of 10, Exceptional, (6 reviews)
"All was amazing!"
United States
Alysha B.
$965 nightly
The price is $1,075
Aug 30 - Aug 31
Total with taxes and fees
Family-Friendly Canal Retreat with Pool and Steps to the Beach

7. 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, (28 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.
$599 nightly
The price is $667
Sep 14 - Sep 15
Total with taxes and fees
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

8. 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, (177 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.
$717 nightly
The price is $799
Sep 19 - Sep 20
Total with taxes and fees
2nd House from the Beach with No Roads to Cross

9. Sea Whisper: North End gem w/ pool & dock

Sea Whisper: North End gem w/ pool & dock
Anna Maria
9.6 out of 10, Exceptional, (71 reviews)
"We loved our stay ! Close to the beach and were able to fish and swim in pool."
United States
Farah S.
$751 nightly
The price is $836
Aug 25 - Aug 26
Total with taxes and fees
Sea Whisper: North End gem w/ pool & dock

10. 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, (18 reviews)
"We had an amazing stay! The house was perfect for our family. The pool and the hot tub were fantastic! We also loved that it was within walking distance to two scoops!"
United States
Aaron Z.
$1,293 nightly
The price is $1,440
Aug 31 - Sep 1
Total with taxes and fees
Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

11. 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, (71 reviews)
"This house is in an excellent location halfway between the bay and the gulf, on a street very close to dining, shopping, etc. and yet quiet. Took only four minutes to walk to coffee shop, eight minutes to the beach and restaurants. House was perfect for our family weekend vacation. We all enjoyed the pool. Washer/dryer on site was convenient. Check in was super easy with door code. Property was clean. Everything worked out well, no issues."
United States
Teresa
$774 nightly
The price is $861
Sep 22 - Sep 23
Total with taxes and fees
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

12. 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, (44 reviews)
"Excellent customer service from the management company. Clean home, well stocked with dishes, comfortable beds."
United States
Lisa B.
$777 nightly
The price is $869
Aug 26 - Aug 27
Total with taxes and fees
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

13. 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.
$599 nightly
The price is $667
Aug 25 - Aug 26
Total with taxes and fees
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

14. Palmetto Sunset -Heat Pool/Spa, Steps to Beach!

Palmetto Sunset -Heat Pool/Spa, Steps to Beach!
Anna Maria
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at Palmetto Sunset! The house was exactly as pictured and the location was wonderful - steps to the beach and right around the corner from restaurants. "
United States
Lyndsey P.
$1,191 nightly
The price is $1,327
Aug 30 - Aug 31
Total with taxes and fees
Palmetto Sunset -Heat Pool/Spa, Steps to Beach!

15. Gulf View Retreat! Pool, Decks and 2 King Beds!

Gulf View Retreat! Pool, Decks and 2 King Beds!
Anna Maria
9.6 out of 10, Exceptional, (28 reviews)
"Clean, comfortable, great location. "
United States
Matthew R.
$997 nightly
The price is $1,111
Aug 27 - Aug 28
Total with taxes and fees
Gulf View Retreat! Pool, Decks and 2 King Beds!

16. 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, (21 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
$600 nightly
The price is $668
Sep 14 - Sep 15
Total with taxes and fees
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

17. 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
9.8 out of 10, Exceptional, (40 reviews)
"Amazing stay! location was perfect, the unit was clean and the host was so kind/accommodating!"
United States
Kyle K.
$425 nightly
The price is $474
Sep 14 - Sep 15
Total with taxes and fees
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

18. Covey Cottage! Walk to Beach, Boutique Shops and City Pier

Covey Cottage! Walk to Beach, Boutique Shops and City Pier
Anna Maria
9.8 out of 10, Exceptional, (65 reviews)
"Perfect house with amazing backyard and pool in a great location! We had the best time and can’t wait to come back!"
United States
Kristen D.
$752 nightly
The price is $839
Sep 20 - Sep 21
Total with taxes and fees
Covey Cottage! Walk to Beach, Boutique Shops and City Pier

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

Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B
Anna Maria
9.8 out of 10, Exceptional, (32 reviews)
"Great location and beautiful accommodations!"
United States
Daniela S.
$528 nightly
The price is $588
Aug 27 - Aug 28
Total with taxes and fees
Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

20. 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, (32 reviews)
"Great place to stay!Nice walk to the beach!"
United States
Rose Y.
$435 nightly
The price is $485
Sep 18 - Sep 19
Total with taxes and fees
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
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

Price trends for vacation rentals in Anna Maria

Less expensive
More expensive
Next month
September
March
$540
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 $460 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 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 602 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.