Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (159)
"This property checked off the boxes for a wonderful generational trip for the girls. It was clean, beach access was so private, and the deck furniture worked well for our needs. Baby gate was helpful. All equipment was working and the air conditioning unit was very good and kept us cool on the warmer days. Location was great! The pier was a close walk and instacart delivers to the address so no leaving for groceries!"
The price is AU$1,252
per night
2 June - 3 June
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Shower, hair dryer, towels, soap
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
10.0 out of 10, Exceptional, (27)
"The place roomy, clean, well stocked. Perfect for our week at the beach. I do wish the screened porch was fully screened. There is a spiral staircase that goes to the pool from the screened porch and it allows mosquitoes to enter the area."
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Vibrant Island Home w/ Pool, 1 Block to Beach
Property grounds
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (28)
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
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Blue Lagoon North by SeaBreeze Vacation
Beach nearby
Blue Lagoon North by SeaBreeze Vacation
9.8 out of 10, Exceptional, (24)
"Very nice and clean. Fully equipped with beach cart and umbrellas"
Blue Lagoon North by SeaBreeze Vacation
BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi/Trolley, Dog*(See...
Exterior
BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi/Trolley, Dog*(See...
9.8 out of 10, Exceptional, (26)
"Fabulous panoramic view! Great layout."
BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi/Trolley, Dog*(See...
Charming cottage in quiet area, close to beach & bay.
Beach nearby, sun-loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
9.8 out of 10, Exceptional, (234)
"This charming 2 bed, 1 bath cottage is in the perfect location. It is in walking distance to coffee shops, breakfast spots and dinner restaurants. Close to the beach one direction and city pier the other. It is well stocked with all you would need and exceptionally clean. The screened porch in back with solar lighting in the back yard is ideal for your evening glass of wine! Definitely recommend!"
Charming cottage in quiet area, close to beach & bay.
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
Pool
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
10.0 out of 10, Exceptional, (97)
"This was our 2nd year staying at Rum Cove and we would definitely book this house again. The property managers were very responsive to one minor issue that we had on check in. The house is in walking distance to the beach, the pier and many restaurants and shops."
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
Aerial view
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
10.0 out of 10, Exceptional, (167)
"We loved the location. Very walkable to the pier, beach, restaurants/shopping. Bungalow is tucked away with great privacy."
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
Charming house with private heated pool, lanai. Great location to beach & shops
Beach nearby, sun-loungers, beach towels
Charming house with private heated pool, lanai. Great location to beach & shops
10.0 out of 10, Exceptional, (145)
"Your home was all that we needed and then some. It was a nice break to get away from the rainy cool weather in New York. We had a wedding to go to and it was from walking distance so that was a plus. Never been to the west side of Florida before let alone the island. Beautiful and breathtaking. Thanks again."
Charming house with private heated pool, lanai. Great location to beach & shops
Adorable luxury Resort Unit in a perfect location! Great Pool area!
Beach nearby
Adorable luxury Resort Unit in a perfect location! Great Pool area!
9.6 out of 10, Exceptional, (49)
"Nice unit, but a bit difficult without a washer and dryer in the unit and one can easily be put in in the closet of the main bedroom. We asked for more towels and were told they would be coming, but none were delivered. The kitchen was nicely equipped with what we needed and we liked the pool, outdoor patio, and proximity to the pier. Thank you for a lovely stay."
The price is AU$1,013
per night
3 June - 4 June
Adorable luxury Resort Unit in a perfect location! Great Pool area!
Bean Point Gem awaits your stay!
Beach nearby, sun-loungers, beach towels
Bean Point Gem awaits your stay!
9.6 out of 10, Exceptional, (170)
"We celebrated our daughter’s high school graduation. It was a wonderful week for our family to be together. The property is amazing and so close to the beach and food/shops. We can’t wait to come back!"
Bean Point Gem awaits your stay!
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
Fridge, microwave, oven, stovetop
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
10.0 out of 10, Exceptional, (75)
"A wonderful stay at a high quality house. Great amenities and quality furnishings throughout. Also a fantastic location. Would highly recommend."
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
Lake La Vista Beach House
Beach nearby
Lake La Vista Beach House
9.2 out of 10, Wonderful, (20)
"We loved this property, would book with SATO again :)"
Lake La Vista Beach House
Beach Bay Serenity: Pine Ave canal front pool home
A heated pool
Beach Bay Serenity: Pine Ave canal front pool home
10.0 out of 10, Exceptional, (21)
"Great location and great property! Looking forward to a future visit."
Beach Bay Serenity: Pine Ave canal front pool home
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
Pool
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
10.0 out of 10, Exceptional, (179)
"This year two for us and we adore this villa whenever we visit AMI. It's a solid 5/5 across the board. With the boat dock, mornings are effortless; we wake up, get ready, hop on the boat and head straight to the beach or fishing spots. Giovanna, the host, is fantastic; communication with her is top-notch. The house easily accommodates our entire family. Looking forward to returning in the future!"
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
Beach
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
8.8 out of 10, Excellent, (28)
"Great location about 5 min drive to north Anna Maria beach or 10 min walk to the bay side for beach. Loved getting to walk to several local restaurants and would definitely recommend trying Ginny’s and Jane E’s for pastries and coffee."
The price is AU$725
per night
5 June - 6 June
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
Beach nearby, sun-loungers, beach towels
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
9.8 out of 10, Exceptional, (64)
"This was our third stay at Boathouse Cottage and it never disappoints. Stocked with everything you need for your stay. Short stroll to the beach. We love the private pool. The pool is in the sun all day. A lot of the rentals have shaded pool areas which is not what I want coming from the north! We have already booked again for next year, we can’t wait!"
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
Going Coastal by SeaBreeze Vacation
Beach nearby
Going Coastal by SeaBreeze Vacation
9.8 out of 10, Exceptional, (19)
"Location 10/10, but lots of little annoying things such as most of the crockery and glassware is poor quality and is chipped. None of it matches. All of it was sub standard and not something we’d have in our own home. We had to wash all crockery before using it as it was grubby. The cutlery, pots pans, coffee machine (rusty) are old and need replacing. The sliding glass doors are dirty as is the outside covered dining area. Pool area and dock is excellent. The area is quiet. Lots of beach...
Going Coastal by SeaBreeze Vacation
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Pool
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
9.8 out of 10, Exceptional, (37)
"Love everything about this place! Great location! Close to beach, close to shopping, close to restaurants!! What more could we ask for! Will be back!!"
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
A heated pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, (100)
"We enjoyed our stay at Bay - Canal Waterfront! We enjoyed the amenities - the pool is beautiful, large and in the sun all day but plenty of shady areas if you want that too. The kayaks were enjoyed as well and we did have some manatee sightings! We enjoyed the golf cart as well! The layout of the house is 2 separate areas with a full unit on top and on bottom. The only complaint we had which cannot be controlled by the owner is the smell of the muck that congregates at the end of the canal which...
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
Don't see what you're looking for?
See all available properties in Anna Maria
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.

Anna Maria Holiday Home Travel Info

Number of holiday homes
1 579
Popular accommodation
Anna Maria private holiday homes
Known landmarks
Coquina Beach, Anna Maria Beach and Brandenton Beach
International airports
Tampa, FL (TPA-Tampa Intl.) and Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)

Other types of properties in Anna Maria you may be interested in

Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (159)
"This property checked off the boxes for a wonderful generational trip for the girls. It was clean, beach access was so private, and the deck furniture worked well for our needs. Baby gate was helpful. All equipment was working and the air conditioning unit was very good and kept us cool on the warmer days. Location was great! The pier was a close walk and instacart delivers to the address so no leaving for groceries!"
The price is AU$1,252
per night
2 June - 3 June
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Shower, hair dryer, towels, soap
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
10.0 out of 10, Exceptional, (27)
"The place roomy, clean, well stocked. Perfect for our week at the beach. I do wish the screened porch was fully screened. There is a spiral staircase that goes to the pool from the screened porch and it allows mosquitoes to enter the area."
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Vibrant Island Home w/ Pool, 1 Block to Beach
Property grounds
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (28)
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block 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.

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$725 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?

Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog: This highly rated holiday home rental in Anna Maria is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Other favourite homes for rent in Anna Maria are Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay and Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart.

How many holiday rentals are there in Anna Maria?

With 841 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 Bradenton Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places such as Fort De Soto Park and Lido Beach.

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.

Recent reviews of Anna Maria properties
Expedia verified reviews

Bean Point Gem awaits your stay!

Bean Point Gem awaits your stay!

5/5 Excellent
Graduation Getaway
"We celebrated our daughter’s high school graduation. It was a wonderful week for our family to be together. The property is amazing and so close to the beach and food/shops. We can’t wait to come back!"
A verified traveller stayed at Bean Point Gem awaits your stay!
Posted 4 days ago
Bean Point Gem awaits your stay!