Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

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 reviews
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
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, 168 reviews
"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!
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 reviews
"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 NZ$1,073
per night
5 Jun - 6 Jun
Adorable luxury Resort Unit in a perfect location! Great Pool area!
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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 reviews
"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 NZ$1,326
per night
12 Jun - 13 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
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 reviews
"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
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 reviews
"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!
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 reviews
"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
2nd House from the Beach with No Roads to Cross
On the beach
2nd House from the Beach with No Roads to Cross
10.0 out of 10, Exceptional, 156 reviews
"Excellent stay. Beautiful clean property. Location is amazing. Fantastic communication with host Stephanie."
The price is NZ$2,438
per night
8 Jun - 9 Jun
2nd House from the Beach with No Roads to Cross
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, 146 reviews
"Great vacation home equipped with anything you might need for fun and relaxation. Easy access to beach and nearby shops. Ideal for families . Stocked with games , beach and pool supplies. Immaculately clean and welcoming!"
Charming house with private heated pool, lanai. Great location to beach & shops
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 reviews
"Great location and great property! Looking forward to a future visit."
Beach Bay Serenity: Pine Ave canal front pool home
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
A heated pool
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
9.2 out of 10, Wonderful, 39 reviews
"Surreal Soulshine! We had the pleasure of staying at Soulshine for the month of February. This was our first time coming to AMI and won’t be our last. Everything from booking to check in was flawless. The location was perfect, a short walk to the gulf, bay, shopping and dining. The house was well appointed with everything we needed to make this house a home. The views from every deck were fabulous and the outdoor entertainment area was a bonus. Can’t wait to return to our new found paradise!"
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
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 reviews
"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
Private Home 1 Block to Beach with Pool and Hot Tub!
Fridge, microwave, oven, stovetop
Private Home 1 Block to Beach with Pool and Hot Tub!
9.8 out of 10, Exceptional, 33 reviews
"Great home with everything needed for the beach, great location and communication with property management."
The price is NZ$1,884
per night
7 Jun - 8 Jun
Private Home 1 Block to Beach with Pool and Hot Tub!
Blue Lagoon North by SeaBreeze Vacation
Beach nearby
Blue Lagoon North by SeaBreeze Vacation
9.8 out of 10, Exceptional, 24 reviews
"Very nice and clean. Fully equipped with beach cart and umbrellas"
Blue Lagoon North by SeaBreeze Vacation
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 reviews
"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 NZ$768
per night
5 Jun - 6 Jun
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
Beach nearby, sun-loungers, beach towels
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
10.0 out of 10, Exceptional, 104 reviews
"Great place to stay for 2 people, very nice. Perfect location for people that prefer the north end of the island!"
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
Fridge, microwave, oven, stovetop
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
9.8 out of 10, Exceptional, 31 reviews
"great house, great location, use of dock is a plus. air condition has issues of family area is cool but ALL bedrooms are extremely hot at all times!!"
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Beach nearby, sun-loungers
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
10.0 out of 10, Exceptional, 12 reviews
"Our short stay was excellent!! So clean with friendly people. Also so close to the beach. Everything was wonderful!"
The price is NZ$861
per night
12 Jun - 13 Jun
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Spacious, Desirable North-End Gem on Canal w/ Dock & Heated Pool
Beach nearby, sun-loungers, beach towels
Spacious, Desirable North-End Gem on Canal w/ Dock & Heated Pool
9.8 out of 10, Exceptional, 99 reviews
"We had such a relaxing week. The pool was nice and warm. The house was comfy and well equipped. Nice neighborhood close to everything you could need."
Spacious, Desirable North-End Gem on Canal w/ Dock & Heated Pool
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
Exterior
Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
10.0 out of 10, Exceptional, 75 reviews
"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
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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.

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

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 reviews
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
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, 168 reviews
"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!
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 reviews
"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 NZ$1,073
per night
5 Jun - 6 Jun
Adorable luxury Resort Unit in a perfect location! Great Pool area!
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Anna Maria holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Anna Maria. 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 Anna Maria. 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 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 holiday 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 Anna Maria short-term rentals, that won’t be hard to do.

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

Charming house with private heated pool, lanai. Great location to beach & shops

Charming house with private heated pool, lanai. Great location to beach & shops

5/5 Excellent
Beach Vacation
"Great vacation home equipped with anything you might need for fun and relaxation. Easy access to beach and nearby shops. Ideal for families . Stocked with games , beach and pool supplies. Immaculately clean and welcoming!"
A verified traveller stayed at Charming house with private heated pool, lanai. Great location to beach & shops
Posted 3 days ago
Charming house with private heated pool, lanai. Great location to beach & shops