Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

Bo’s Beach Bungalow! Steps to Beach, Shops and Dining
8.6 out of 10, Excellent, (4)
"Nice quiet area. About a block from beach! Short walk to Pine Ave with many restaurants and shops. House was nothing fancy but clean and comfortable. Had everything we needed. Only compliant was could use some more silverware. Hope it's available for us next year!"
The price is AU$437
includes taxes & fees
20 Oct - 21 Oct
Bo’s Beach Bungalow! Steps to Beach, Shops and Dining
Emerald Shores East! Walk to Beach!
2.5 star property
9.6 out of 10, Exceptional, (4)
"It was good "
The price is AU$604
includes taxes & fees
19 Oct - 20 Oct
Emerald Shores East! Walk to Beach!
Beautiful Bungalow with Pool and Bay Views! - Barefoot by the Bay at Bayside Bun
9.8 out of 10, Exceptional, (36)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
The price is AU$608
includes taxes & fees
19 Oct - 20 Oct
Beautiful Bungalow with Pool and Bay Views! - Barefoot by the Bay at Bayside Bun
Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (39)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
Adorable Cottage with Covered Balconies and Private Pool
Feelin' Salty-Pool Modern Beach House w/Pool/Spa
10.0 out of 10, Exceptional, (4)
"We had a great stay at Feelin Salty. The pool and hot tub were an awesome touch. Would recommend to stay! "
The price is AU$1,110
includes taxes & fees
19 Oct - 20 Oct
Feelin' Salty-Pool Modern Beach House w/Pool/Spa
Beachside Duplex w/ Pool and Private Suite
2.5 star property
8.0 out of 10, Very good, (1)
"We have stayed here over the years and have enjoyed the perfect location to the beach. The house is a bit dated and needs a few upgrades but overall the house was very clean and comfortable. Please note there were no beach umbrellas supplied but did have plenty of beach chairs. You may want to plan on alternate shade options once there as the sun is intense and can be challenging. We would stay there again as the price was very affordable. "
The price is AU$602
includes taxes & fees
20 Oct - 21 Oct
Beachside Duplex w/ Pool and Private Suite
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
9.6 out of 10, Exceptional, (19)
"Convenient to the beach, nicely furnished inside."
The price is AU$786
includes taxes & fees
29 Oct - 30 Oct
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Beautiful Condo on Pine Ave, 2 Blocks to Beach
8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
The price is AU$700
includes taxes & fees
19 Oct - 20 Oct
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
8.6 out of 10, Excellent, (42)
"Nice place for long weekend. Close to great restaurants and an easy walk to the beach."
The price is AU$510
includes taxes & fees
19 Oct - 20 Oct
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Cute Cottage Near Beach and Shops
10.0 out of 10, Exceptional, (2)
"Beautiful home! So close to the beach, coffee, and shops. Will be back!"
The price is AU$575
includes taxes & fees
19 Oct - 20 Oct
Cute Cottage Near Beach and Shops
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
10.0 out of 10, Exceptional, (35)
"Perfect, cutest cottage within steps of the beach."
The price is AU$736
includes taxes & fees
19 Oct - 20 Oct
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
9.8 out of 10, Exceptional, (28)
"Perfect accommodations and location for family of four with two boys ages 5 7. Property was extremely clean and in a great location! Can't wait to come back."
The price is AU$757
includes taxes & fees
19 Oct - 20 Oct
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Covey Cottage! Walk to Beach, Boutique Shops and City Pier
9.8 out of 10, Exceptional, (52)
"Great location. The cottage was very clean and well equipped. Would definitely stay there again."
The price is AU$768
includes taxes & fees
18 Oct - 19 Oct
Covey Cottage! Walk to Beach, Boutique Shops and City Pier
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
9.6 out of 10, Exceptional, (31)
"Great location, cool little property and cabin. Perfect for a long weekend getaway!"
The price is AU$765
includes taxes & fees
27 Oct - 28 Oct
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Canal Home with Pool & Dock Near Beach
9.6 out of 10, Exceptional, (7)
"The only negative I can say is that my trip wasn't longer. This property is fantastic. Great location and had everything we needed. I would highly recommend it and can't wait to book it again!"
Canal Home with Pool & Dock Near Beach
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
8.2 out of 10, Very good, (28)
"For our small family of 3 this was the perfect little condo that is located in my favorite area of the island. Everything we needed was a short bike ride away. "
The price is AU$581
includes taxes & fees
21 Oct - 22 Oct
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Beautiful Guest House Near the Beach with Private Pool!
8.6 out of 10, Excellent, (29)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
The price is AU$708
includes taxes & fees
20 Oct - 21 Oct
Beautiful Guest House Near the Beach with Private Pool!
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
8.6 out of 10, Excellent, (37)
"Very close to the beach and restaurants!"
The price is AU$641
includes taxes & fees
20 Oct - 21 Oct
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
9.6 out of 10, Exceptional, (59)
"Everything is just perfect,I love all about this house, ♥️♥️♥️"
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Adorable Cottage moments to beach w/ pool, beach gear, bikes
9.8 out of 10, Exceptional, (11)
"Loved how the cottage is wqlking distance to the beach and also restaurants."
The price is AU$904
includes taxes & fees
29 Oct - 30 Oct
Adorable Cottage moments to beach w/ pool, beach gear, bikes
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 favourite 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 depend 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 AU$670 per night. Entering your travel dates in the search wizard might find you 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?

Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt: This highly rated holiday home rental in Anna Maria offers an outdoor pool, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and 1 hot tub. Other favourite homes for rent in Anna Maria are Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier! and Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!.

How many holiday rentals are there in Anna Maria?

With 794 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.