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Check prices for these dates

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
9.8 out of 10, Exceptional, (45 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 £392
includes taxes & fees
8 Nov - 9 Nov
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, (59 reviews)
"Great bungalow in perfect location"
United States
David V.
The price is £378
includes taxes & fees
17 Nov - 18 Nov
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

3. 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, (31 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
The price is £408
includes taxes & fees
15 Nov - 16 Nov
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

4. 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
9.2 out of 10, Wonderful, (108 reviews)
"It is a very nice little unit. Recently renovated and comfortable. We had some problems with the front door lock that they are aware of, so it took a bit of time to initially enter the property. If the upper floor is occupied, it is a bit noisy from the activity overhead. The location is very good for walking to restaurants and shops. The Waterfront Restaurant is excellent!"
United States
Rick C.
The price is £357
includes taxes & fees
8 Nov - 9 Nov
Updated bayside condo with heated pool - across the street from the beach

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

Anna Maria Beach Cottage 110G Updated cottage, with pool, bikes and beach gear!
Anna Maria
9.6 out of 10, Exceptional, (34 reviews)
"Great little cottage"
United States
Kathy R.
The price is £411
includes taxes & fees
8 Nov - 9 Nov
Anna Maria Beach Cottage 110G Updated cottage, with pool, bikes and beach gear!

6. 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, (34 reviews)
"We loved our stay at 107A! It was perfect for the two of us, We loved the short walk to the beach and how walkable it was to local restaurants and stores. Thank you for a great stay!"
United States
Kathryn M.
The price is £398
includes taxes & fees
14 Nov - 15 Nov
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

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

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
9.6 out of 10, Exceptional, (110 reviews)
"This place was close to the pier, so it was fun watching the construction. You really need to rent a golf cart if staying very long there. Pool was right outside the door! We used the free bus to go to Holmes Beach!"
United States
Jena J.
The price is £357
includes taxes & fees
11 Nov - 12 Nov
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

8. Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!

Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!
Anna Maria
10.0 out of 10, Exceptional, (30 reviews)
"Great property!"
United States
Jessica S.
The price is £464
includes taxes & fees
1 Dec - 2 Dec
Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!

9. 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
9.8 out of 10, Exceptional, (55 reviews)
"Great place for a beach stay on Anna Maria!!!"
United States
John F.
The price is £396
includes taxes & fees
9 Nov - 10 Nov
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

10. 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, (2 reviews)
"We came in for a girls trip and the home and location were perfect. The house is truly steps from the beach and has everything you need. We also enjoyed to pool and patio for coffee and drinks every day."
United States
Holly F.
The price is £562
includes taxes & fees
2 Dec - 3 Dec
Private Pool / Spa Home - Steps to Anna Maria Island Beach

11. 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)
"Has a beautiful view of the bay right behind the houseNeighbors were very friendly,has a new house being built next door but it still was quaint beach was in walking distance. Definitely a must do again."
United States
Terrence H.
The price is £453
includes taxes & fees
8 Nov - 9 Nov
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

12. 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, (24 reviews)
"Great place to stay! Proximity to the beach cannot be beat! Staff was so nice and helpful. Can’t wait to stay again!"
United States
Anne B.
The price is £461
includes taxes & fees
30 Nov - 1 Dec
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

13. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Great sister stayHouse was perfect, pool was enjoyed by us all after a day a the beachMorning and evening at the pool We will be back for our next get together"
United States
Cheryl M.
The price is £568
includes taxes & fees
2 Dec - 3 Dec
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

14. Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Anna Maria
9.2 out of 10, Wonderful, (63 reviews)
"Great place- close to the beach!"
United States
Jaymi R.
The price is £514
includes taxes & fees
8 Nov - 9 Nov
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

15. The Hideaway ~ Near Beach ~ Coastal Cottage

The Hideaway ~ Near Beach ~ Coastal Cottage
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great. So close to the beach a 3 min walk. We loved everything about it."
United States
JASON G.
The price is £643
includes taxes & fees
15 Nov - 16 Nov
The Hideaway ~ Near Beach ~ Coastal Cottage

16. Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave

Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"."
United States
Richard
The price is £546
includes taxes & fees
1 Dec - 2 Dec
Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave

17. 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, (15 reviews)
"Close walk to the beach "
United States
Zev C.
The price is £484
includes taxes & fees
8 Nov - 9 Nov
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

18. Kiwi Cottage ~ Near Beach ~ Heated Pool

Kiwi Cottage ~ Near Beach ~ Heated Pool
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
The price is £585
includes taxes & fees
28 Nov - 29 Nov
Kiwi Cottage ~ Near Beach ~ Heated Pool

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

Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl
Anna Maria
9.8 out of 10, Exceptional, (31 reviews)
"The house was recently remodeled and in amazing condition. It was very clean and the shed had tons of beach gear to use."
United States
Ashley S.
The price is £561
includes taxes & fees
10 Nov - 11 Nov
Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl

20. Fish, Swim & Unwind: Anna Maria Apt Steps to Beach

Fish, Swim & Unwind: Anna Maria Apt Steps to Beach
4.0 star property
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"I can’t believe I forgot to do a review. Let me just get right to it…I love this place. It was so comfortable and clean and a convenient walk to the beach. I wouldn’t want to stay anywhere else when I visit. Very very Comfortable and Convenient!!"
United States
Jhinji
The price is £486
includes taxes & fees
10 Nov - 11 Nov
Fish, Swim & Unwind: Anna Maria Apt Steps to 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.

Find holiday rentals that suit your style

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, apart-hotels, 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 £357 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.

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 574 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.