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

Anna Maria Holiday Rentals

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Our top choices for Anna Maria holiday 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 NZ$818
includes taxes & fees
30 Sept - 1 Oct
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 NZ$801
includes taxes & fees
30 Sept - 1 Oct
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 NZ$856
includes taxes & fees
28 Sept - 29 Sept
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 NZ$836
includes taxes & fees
27 Sept - 28 Sept
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 NZ$856
includes taxes & fees
25 Sept - 26 Sept
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 NZ$826
includes taxes & fees
28 Sept - 29 Sept
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)
The price is NZ$1,011
includes taxes & fees
27 Sept - 28 Sept
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)
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 NZ$775
includes taxes & fees
3 Oct - 4 Oct
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 NZ$1,480
includes taxes & fees
29 Sept - 30 Sept
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 NZ$776
includes taxes & fees
27 Sept - 28 Sept
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 NZ$1,134
includes taxes & fees
7 Oct - 8 Oct
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 NZ$1,154
includes taxes & fees
3 Oct - 4 Oct
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 NZ$1,536
includes taxes & fees
26 Sept - 27 Sept
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 NZ$1,289
includes taxes & fees
5 Oct - 6 Oct
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 NZ$1,022
includes taxes & fees
25 Sept - 26 Sept
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 NZ$1,146
includes taxes & fees
25 Sept - 26 Sept
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 NZ$1,362
includes taxes & fees
29 Sept - 30 Sept
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 NZ$1,482
includes taxes & fees
27 Sept - 28 Sept
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 NZ$1,287
includes taxes & fees
4 Oct - 5 Oct
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

Everything you need to know about Anna Maria holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna Maria holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria holiday rentals we have selected for you start as low as NZ$1,287 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anna Maria rentals

At Expedia, we put the best Anna Maria holiday 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 holiday.

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. 

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Frequently asked questions

Can I find a holiday rental in Anna Maria?

Yes, there are holiday rentals close to the most popular sights in Anna Maria, or you can select 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 holiday rentals that Anna Maria has to offer?

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!: This highly rated holiday home rental in Anna Maria is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite 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 holiday rentals are there in Anna Maria?

With 590 Expedia holiday rentals, you're guaranteed 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 such as Lido Beach and Tampa Bay.

What are holiday rentals like in Anna Maria?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Anna Maria. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.