Anna Maria Island Holiday Rentals

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Holiday Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (286)
"This was an amazing property and we can’t wait to come back on our next trip to the island."
Pelican Post at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3.0 star property
8.8 out of 10, Excellent, (23)
"Great location"
Seabreeze at Anna Maria Island Inn

Bridgewalk A Landmark Resort

3.5 star property
9.2 out of 10, Wonderful, (730)
"We loved the remodeling and location. We only stayed one night but the room was amazing with enough space for a family four. Can't wait to stay again."
The price is NZ$473
includes taxes & fees
7 Aug - 8 Aug
Bridgewalk A Landmark Resort

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (57)
"This house was perfect for our family of 4. Loved the open concept. The small pool was refreshing and the location was amazing - so close to the most beautiful section of the beach. We will be back! "
The price is NZ$1,733
includes taxes & fees
1 Aug - 2 Aug
Adorable Beach cottage just steps Bean Point beach!

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (381)
"Great experience! We loved staying here. This is our second time coming and it never disappoints "
Tradewinds Beach Resort

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

9.6 out of 10, Exceptional, (37)
"Dolphins everyday. Great spot. Can’t really think of any negatives. Really a nice place."
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

Beachfront Home | Pool + Spa | Games | Ocean Views

10.0 out of 10, Exceptional, (38)
"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"
Beachfront Home | Pool + Spa | Games | Ocean Views

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10.0 out of 10, Exceptional, (178)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

3.0 star property
9.2 out of 10, Wonderful, (10)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (222)
"This is a great condo. Super clean, super spacious. Host was very responsive. It’s right across the street from the beach. I highly recommend and would stay again."
The price is NZ$705
includes taxes & fees
3 Aug - 4 Aug
Anna Maria Beach Condo 1/1

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (230)
"Room was clean and comfortable. Spacious enough for 2 people. Nice pool. Will stay here again."
The price is NZ$436
includes taxes & fees
17 Aug - 18 Aug
Anna Maria Sunsets - studio

Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

10.0 out of 10, Exceptional, (1)
"Exceptional property! We truly had the most amazing stay. The property is so beautiful and clean. It has a ton of charm, and the view off the entire back of the home of the emerald green bay is unmatched!Between waking up to amazing sunrises, hearing the sound of the water, while enjoying the bay breeze and watching all of the dolphins swim by, it was one of the most serene and tranquil experiences. The pool and spa are brand new and we loved having options to swim in the pool, paddle board...
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!

9.6 out of 10, Exceptional, (10)
"We loved our time here and can’t wait to book it for next year!"
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (133)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168

~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~

10.0 out of 10, Exceptional, (84)
"Really enjoy this area of the island. Plenty to walk to and most nearby have recovered pretty well from hurricanes. Nice condo with everything needed for a great week getaway from the cold winter"
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~

🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

10.0 out of 10, Exceptional, (86)
"We have stayed in this house a couple of times and love the location the food, shopping and the beach! The backyard oasis is perfect for lounging after a day at the beach. Frankie is fabulous to work with and keeps the property in beautiful condition. Would certainly recommend!"
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

The price is NZ$2,632
includes taxes & fees
17 Aug - 18 Aug
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!

9.0 out of 10, Wonderful, (38)
"Great location, great amenities, and great communication from Mike Norman Realty. "
Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (271)
"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

9.8 out of 10, Exceptional, (56)
"We had an amazing stay! Can’t wait to return!"
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
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 Island Hotel Reviews