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. 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
The price is CA $224
CA $662 total
includes taxes & fees
Sep 24 - Sep 25
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

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

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria
9.8 out of 10, Exceptional, (57 reviews)
"Great stay. "
United States
courtneyharned
The price is CA $223
CA $643 total
includes taxes & fees
Sep 24 - Sep 25
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

3. 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.
The price is CA $234
CA $694 total
includes taxes & fees
Sep 27 - Sep 28
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

4. 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.
The price is CA $229
CA $678 total
includes taxes & fees
Sep 27 - Sep 28
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

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

Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
Anna Maria
9.6 out of 10, Exceptional, (30 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
The price is CA $234
CA $694 total
includes taxes & fees
Sep 24 - Sep 25
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

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

Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Anna Maria
9.6 out of 10, Exceptional, (50 reviews)
"Yes! The cottage was nicely decorated and we had everything we needed for our 2 night stay"
United States
J I.
The price is CA $229
CA $668 total
includes taxes & fees
Sep 28 - Sep 29
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

7. 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.
The price is CA $286
CA $817 total
includes taxes & fees
Sep 28 - Sep 29
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

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

Dog friendly cottage - One block to the Bay!
Anna Maria
9.6 out of 10, Exceptional, (15 reviews)
"Great location!"
United States
Jennifer L.
The price is CA $216
CA $804 total
includes taxes & fees
Sep 24 - Sep 25
Dog friendly cottage - One block to the Bay!

9. Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
The price is CA $181
CA $644 total
includes taxes & fees
Oct 3 - Oct 4
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

10. 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.
The price is CA $303
CA $1,192 total
includes taxes & fees
Sep 29 - Sep 30
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

11. Updated bayside condo with heated pool - across the street from the beach

Updated bayside condo with heated pool - across the street from the beach
Anna Maria
The price is CA $181
CA $627 total
includes taxes & fees
Sep 27 - Sep 28
Updated bayside condo with heated pool - across the street from the beach

12. Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit

Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
Anna Maria
9.4 out of 10, Exceptional, (32 reviews)
"We really enjoyed our stay. The location was perfect- super close to a quiet beach, and close to restaurants and shopping on Pine street. Place was clean and comfortable and had everything we needed to enjoy the beach."
United States
Louise W.
The price is CA $233
CA $913 total
includes taxes & fees
Oct 7 - Oct 8
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit

13. 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.
The price is CA $369
CA $936 total
includes taxes & fees
Sep 24 - Sep 25
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

14. Luxury North End Escape | 3 king beds + pool/spa

Luxury North End Escape | 3 king beds + pool/spa
Anna Maria
9.8 out of 10, Exceptional, (10 reviews)
"Great place! "
United States
Kim K.
The price is CA $270
CA $1,261 total
includes taxes & fees
Sep 26 - Sep 27
Luxury North End Escape | 3 king beds + pool/spa

15. Emerald Shores East! Walk to Beach!

Emerald Shores East! Walk to Beach!
Anna Maria
9.0 out of 10, Wonderful, (12 reviews)
"Clean spot and a great stay. Amazing location and 10/10 service / review. "
United States
Christopher B.
The price is CA $227
CA $1,047 total
includes taxes & fees
Oct 5 - Oct 6
Emerald Shores East! Walk to Beach!

16. 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.
The price is CA $349
CA $828 total
includes taxes & fees
Sep 24 - Sep 25
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

17. 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.
The price is CA $369
CA $938 total
includes taxes & fees
Sep 24 - Sep 25
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

18. Private Pool / Spa Home - Steps to Anna Maria Island Beach

Private Pool / Spa Home - Steps to Anna Maria Island Beach
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"An absolute gem! This place was perfection and we couldn’t be happier. We are already planning to hopefully come back in 2 years for our next girls trip. It was immaculately clean, beautifully decorated, so close to the beach and great location for shopping/restaurants. They had everything at the property we could think of."
United States
Erin S.
The price is CA $304
CA $1,106 total
includes taxes & fees
Sep 29 - Sep 30
Private Pool / Spa Home - Steps to Anna Maria Island Beach

19. 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.
The price is CA $321
CA $1,224 total
includes taxes & fees
Sep 27 - Sep 28
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

20. 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
The price is CA $386
CA $1,046 total
includes taxes & fees
Oct 4 - Oct 5
SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
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

Find out more about Anna Maria

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Anna Maria. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 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.