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, (287)
"This was an amazing property and we can’t wait to come back on our next trip to the island."
The price is AU$372
includes taxes & fees
1 Sept - 2 Sept
Pelican Post at Anna Maria Island Inn

Bridgewalk A Landmark Resort

3.5 star property
9.2 out of 10, Wonderful, (731)
"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 AU$520
includes taxes & fees
7 Aug - 8 Aug
Bridgewalk A Landmark Resort

Seabreeze at Anna Maria Island Inn

3.0 star property
8.8 out of 10, Excellent, (24)
"Great location"
The price is AU$528
includes taxes & fees
1 Sept - 2 Sept
Seabreeze at Anna Maria Island Inn

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (382)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort

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

9.0 out of 10, Wonderful, (2)
"Well maintained propert and enjoyed our stay."
The price is AU$2,134
includes taxes & fees
1 Sept - 2 Sept
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (57)
"Our family of 6enjoyed our stay!"
Adorable Beach cottage just steps Bean Point beach!

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

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (231)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
The price is AU$355
includes taxes & fees
7 Aug - 8 Aug
Anna Maria Sunsets - studio

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

10.0 out of 10, Exceptional, (273)
"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!

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

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

9.8 out of 10, Exceptional, (11)
"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!!!

1 Block to the Beach - LARGE Private Pool - Newly Renovated 6 Bdrm Luxury House

10.0 out of 10, Exceptional, (103)
"We loved our stay! There was plenty of room for our large e"
1 Block to the Beach - LARGE Private Pool - Newly Renovated 6 Bdrm Luxury House

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

9.8 out of 10, Exceptional, (163)
"The location is just a block from the beach and lots of unique restaurants. The pool area is great!"
The price is AU$1,286
includes taxes & fees
10 Aug - 11 Aug
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

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!

The Pink House Unit B: A Cozy Retreat Steps from the Beach

9.8 out of 10, Exceptional, (86)
"We loved this property, it was cute, cozy & extremely clean. We will definitely be back!!!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach

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

Sunset View 3/2 Pet Friendly, 2 Living Rooms, Pool, Steps from Beach, Beach View

2.0 star property
10.0 out of 10, Exceptional, (19)
"This house was perfection! I want to stay here every single year!"
The price is AU$1,282
includes taxes & fees
13 Aug - 14 Aug
Sunset View 3/2 Pet Friendly, 2 Living Rooms, Pool, Steps from Beach, Beach View

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

9.8 out of 10, Exceptional, (56)
"Great place "
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (223)
"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 AU$512
includes taxes & fees
14 Aug - 15 Aug
Anna Maria Beach Condo 1/1

Vacay in luxury! So close to the beach!

9.8 out of 10, Exceptional, (63)
"Fantastic location, relaxing vibe, absolutely beautiful and perfect location "
The price is AU$721
includes taxes & fees
1 Sept - 2 Sept
Vacay in luxury! So close to the 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.
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Top Anna Maria Island Hotel Reviews