Search Vacation Homes in Anna Maria

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 858 Vacation Homes in Anna Maria with updated reviews, rates, and availability.

Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Fridge, microwave, oven, stovetop

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

8.0 out of 10, Very Good, (67)
"walk to sunset bar with great food, monkey bus will take you anywhere on island quickly!!"
The price is AED 1,102
AED 2,472 total
includes taxes & fees
11 May - 12 May
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Near Bean Point!! Short stays available! Heated Pool
Exterior

Near Bean Point!! Short stays available! Heated Pool

9.4 out of 10, Exceptional, (43)
"Great location, walking distance to beach. Quiet and relaxing. "
Near Bean Point!! Short stays available! Heated Pool
Quiet North End Home Only 2 Blocks to Beach with Private Pool
A heated pool

Quiet North End Home Only 2 Blocks to Beach with Private Pool

9.0 out of 10, Wonderful, (44)
"Clean property and cute inside. The location was fantastic and very quiet area. The pool was lovely and the sound of the waterfall was a nice surprise. I would definitely recommend this property. "
Quiet North End Home Only 2 Blocks to Beach with Private Pool
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!
Aerial view

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

9.6 out of 10, Exceptional, (11)
"Great location, well appointed!"
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!
Bella Vista: Bay front with gorgeous views and outdoor living space.
Terrace/patio

Bella Vista: Bay front with gorgeous views and outdoor living space.

9.4 out of 10, Exceptional, (9)
"It’s the perfect getaway right on the bay, beautiful home with a amazing view. This house has everything we wanted and needed for a wonderful vacation"
Bella Vista: Bay front with gorgeous views and outdoor living space.
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
Sun loungers, beach towels

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

9.8 out of 10, Exceptional, (115)
"The house was perfect. Great location and the outdoor space is phenomenal!"
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!
Beach nearby, sun loungers, beach towels

Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!

9.2 out of 10, Wonderful, (61)
"Fun and convenient location. Nice property. Had a blast."
Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!
The Wee Cottage | House in Anna Maria
TV, DVD player, books, video library

The Wee Cottage | House in Anna Maria

8.4 out of 10, Very Good, (15)
"The Wee cottage was the perfect couple spot. Secluded enough to relax outside, and perfect location to get to the beach within minutes. We can't wait to book again."
The Wee Cottage | House in Anna Maria
Escape to an island adventure!
Interior

Escape to an island adventure!

10.0 out of 10, Exceptional, (113)
"We LOVED our stay here!! It was perfect. Great location and the game room downstairs is so cute.Also, don’t forget they have BIKES!!! Loved!"
Escape to an island adventure!
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island
A heated pool

The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

10.0 out of 10, Exceptional, (16)
"Wonderful time at The TipSea Turtle. The kids had a blast at the pool and playing mini golf!! The beach was close by Thank you"
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island
Golf Cart, Stonehenge by SeaBreeze Vacation
Beach nearby

Golf Cart, Stonehenge by SeaBreeze Vacation

10.0 out of 10, Exceptional, (19)
"Amazing Stay!"
Golf Cart, Stonehenge by SeaBreeze Vacation
MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Exterior

MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (176)
"Although we had not so nice weather we managed to sit and enjoy the view! Lots of fun moments with friends and family. Enjoyed local eateries and shopping. Thanks again!"
The price is AED 1,561
AED 3,358 total
includes taxes & fees
20 May - 21 May
MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
On the beach, sun loungers, beach towels

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

10.0 out of 10, Exceptional, (218)
"This was a beautiful house with an amazing location! We loved our stay!"
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Interior

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

9.8 out of 10, Exceptional, (84)
"We love this house. Great location. The house was clean and the kitchen is well e"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Short stays available! Located on North End of Island.
Exterior

Short stays available! Located on North End of Island.

9.2 out of 10, Wonderful, (49)
"walking distance to beach and Rod Reel Pier was perfect!"
Short stays available! Located on North End of Island.
On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life
Aerial view

On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life

9.6 out of 10, Exceptional, (18)
"This was the perfect place for our family vacation to AMI!"
On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life
Gulf Views 🌊 | Elevator 🏡 | 50 Yards to Beach 🌴| Heated Pool & Spa 🌅Sunsets
Beach nearby

Gulf Views 🌊 | Elevator 🏡 | 50 Yards to Beach 🌴| Heated Pool & Spa 🌅Sunsets

10.0 out of 10, Exceptional, (3)
"We were absolutely thrilled with our stay at Shore to Please! The house was impeccably clean, beautifully decorated, and had everything we needed for a comfortable vacation. The location was perfect, close to the beach and local shops, and the hosts were incredibly responsive to any questions we had. We felt truly welcomed and would definitely return for another stay."
Gulf Views 🌊 | Elevator 🏡 | 50 Yards to Beach 🌴| Heated Pool & Spa 🌅Sunsets
OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!
Fridge, microwave, oven, stovetop

OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!

9.8 out of 10, Exceptional, (193)
"Spacious and well equipped house. Great location!"
OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!
Bay Breeze Cottages #3
Beach

Bay Breeze Cottages #3

9.8 out of 10, Exceptional, (110)
"Really enjoyed my stay. Beautiful cottage and scenery."
Bay Breeze Cottages #3
Elevator - A Bean Point Paradise by SeaBreeze Vacation
Beach nearby

Elevator - A Bean Point Paradise by SeaBreeze Vacation

2.5 star property
10.0 out of 10, Exceptional, (3)
"Great location close to beach access. We have stayed on same street before and it was a tad more busy at night with younger crowds making noise. Kitchen has everything and pool is fantastic. Furniture and wear on house has evidence of high traffic but didn’t disrupt our stay. Overall great spot and terrific amenities. "
Elevator - A Bean Point Paradise by SeaBreeze Vacation
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.
Don't see what you're looking for?
See all available properties in Anna Maria
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Anna Maria

Updated bayside condo with heated pool - across the street from the beach
Property grounds

Updated bayside condo with heated pool - across the street from the beach

9.2 out of 10, Wonderful, (86)
"Had a great stay. Highly recommend "
The price is AED 298
AED 1,087 total
includes taxes & fees
11 May - 12 May
Updated bayside condo with heated pool - across the street from the beach
Charming Bungalow with Fabulous Location and Private Pool!
Beach nearby, sun loungers, beach towels

Charming Bungalow with Fabulous Location and Private Pool!

9.8 out of 10, Exceptional, (154)
"715 North Bay Boulevard is a beautiful cottage. This location has everything you will need for a stay, easy access to Bean Point beach access, lots of nice restaurants and beach stores with a short drive. Thank you for sharing your beautiful little home with us. "
The price is AED 1,561
AED 2,991 total
includes taxes & fees
18 May - 19 May
Charming Bungalow with Fabulous Location and Private Pool!
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, (85)
"We had a great vacation at this rental property and will definitely stay here again when we return to Anna Maria island. House is beautiful, location is perfect, and it had everything we needed to make our week in Anna Maria island fun and relaxing. The pool was great, heated to the perfect temperature. Thank you to our great hosts for making our stay a great one! "
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.