Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is NZ$1,359
includes taxes & fees
2 Jun - 3 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Beach nearby, sun-loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (232)
"This adorable little cottage is perfectly located! We could walk to restaurants, the beach and the free trolley. It was quiet and serene! The house was so clean, beautifully decorated and fully stocked! Cindy was a fantastic host! Thank you for helping make our reunion for our 35th anniversary as friends such a special experience. We will definitely be back!"
Charming cottage in quiet area, close to beach & 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)
"We booked this adorable two bedroom duplex for four nights to go to Anna Maria for a family wedding. We had no idea about the island and ended up in the loveliest quiet little neighborhood in beans point. The unit was exactly as it was described and as it looks in the pictures, the owner was incredibly responsive and helpful and I would highly recommend this adorable spot for anyone looking for an affordable, immaculate, quiet place on the island."
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
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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
Shower, hair dryer, towels, soap
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
10.0 out of 10, Exceptional, (25)
"It was a perfect stay at coral cove! Gorgeous home with everything you need for a day at the beach. The short walk to the shore was perfect for us. We loved being able to take a beach break in the afternoon and spend some time in the pool then go back for the sunset. We love staying on the north end, and we will be back!"
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Beach nearby, sun-loungers, beach towels
Bean Point Gem awaits your stay!
9.6 out of 10, Exceptional, (167)
"We thoroughly enjoyed our stay and would book again in a heartbeat. The location is amazing, property was clean and well stocked. Our family loved it!"
Bean Point Gem awaits your stay!
Outdoor pool, a heated pool
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
9.6 out of 10, Exceptional, (65)
"Artsy fun house comfortable and convenient to everything! Clean inside and out for the perfect family beach vacation!! I could live there!!"
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
Beach nearby
Going Coastal by SeaBreeze Vacation
10.0 out of 10, Exceptional, (18)
"Nice intimate place: cozy; perfect for couple, or small family. Easy walk to the Gulf! Nicely situated. Would come again."
Going Coastal by SeaBreeze Vacation
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
Outdoor dining
Beachfront Home with Amazing Deck Views! Near Shops and Restaurants! -High Tide
10.0 out of 10, Exceptional, (12)
"Truly amazing location - right on the beach with amazing swimming and the sound of waves crashing at night. House was beautifully and thoughtfully designed, super clean and comfy! Would definitely come back 😊"
The price is NZ$3,283
includes taxes & fees
24 May - 25 May
Beachfront Home with Amazing Deck Views! Near Shops and Restaurants! -High Tide
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
Beach nearby, sun-loungers, beach towels
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
10.0 out of 10, Exceptional, (140)
"We loved this property! The location is perfect for a close walk to the beautiful beaches. The check in was a breeze. The renters provided everything you could possibly need, so we really ended up packing more than was even necessary. The renters got right back with us when we had a question. There was nothing to complain about with our stay. Thank you for making our vacation great!"
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
Beach
Bay Breeze Cottages #1 (The Mahi-Mahi)
9.8 out of 10, Exceptional, (70)
"Great little place. Nicely updated, very clean, great location. Loved having golf cart included. The pool was wonderful, private, very pretty and lots of patio furniture. Really enjoyed our first stay ion AMI."
Bay Breeze Cottages #1 (The Mahi-Mahi)
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
Property grounds
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
10.0 out of 10, Exceptional, (8)
"Very roomy rental with multiple amenities right in the heart of it all!"
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
Beach nearby
Blue Lagoon North by SeaBreeze Vacation
9.8 out of 10, Exceptional, (24)
"spent an amazing two weeks at Blue Lagoon - first week was just myself and my husband and the 2nd week had 2 good friends join us in our 2 bedroom unit. House was immaculate, perfect location - easy walk to some great restaurants (Waterfront, Sandbar, misc. spots on Pine Street, etc.). We knew the unit was going to be on the small side but had exactly what we needed and though has a shared pool, our duplex neighbors were wonderful and plenty of room to all spread out around the pool. We each had...
Blue Lagoon North by SeaBreeze Vacation
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 NZ$712
includes taxes & fees
22 May - 23 May
Budget-friendly beach condo with pool access, washer/dryer, WiFi & full kitchen
Beach nearby
Northend Anna Maria Island. Private Heated Pool
8.6 out of 10, Excellent, (24)
"House was perfect for our family and it was in a great location for the kids to ride bikes and go To the pier or the beach."
Northend Anna Maria Island. Private Heated Pool
Property grounds
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
9.6 out of 10, Exceptional, (80)
"Easy walk to the pier for evening music and our favorite restaurant The Waterfront, great place for a couple to enjoy the sun, pool and restaurants on the north end without breaking the bank."
The price is NZ$840
includes taxes & fees
2 Jun - 3 Jun
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Property grounds
Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!
9.6 out of 10, Exceptional, (38)
"It was awesome, from the closeness of the Beach, to the pool, and to the sunsets on the roof top, everything was amazing. Thank you for having such a great place to rent."
Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!
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.

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

Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is NZ$1,359
includes taxes & fees
2 Jun - 3 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Beach nearby, sun-loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (232)
"This adorable little cottage is perfectly located! We could walk to restaurants, the beach and the free trolley. It was quiet and serene! The house was so clean, beautifully decorated and fully stocked! Cindy was a fantastic host! Thank you for helping make our reunion for our 35th anniversary as friends such a special experience. We will definitely be back!"
Charming cottage in quiet area, close to beach & 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)
"We booked this adorable two bedroom duplex for four nights to go to Anna Maria for a family wedding. We had no idea about the island and ended up in the loveliest quiet little neighborhood in beans point. The unit was exactly as it was described and as it looks in the pictures, the owner was incredibly responsive and helpful and I would highly recommend this adorable spot for anyone looking for an affordable, immaculate, quiet place on the island."
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
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 cottage in quiet area, close to beach & bay.

Charming cottage in quiet area, close to beach & bay.

5/5 Excellent
Girls' trip weekend
"This adorable little cottage is perfectly located! We could walk to restaurants, the beach and the free trolley. It was quiet and serene! The house was so clean, beautifully decorated and fully stocked! Cindy was a fantastic host! Thank you for helping make our reunion for our 35th anniversary as friends such a special experience. We will definitely be back!"
A verified traveller stayed at Charming cottage in quiet area, close to beach & bay.
Posted 3 days ago
Charming cottage in quiet area, close to beach & bay.