Holiday Homes in Anna Maria Island

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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Holiday Homes in Anna Maria Island and around

🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬
Sun-loungers, beach towels

🏝 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🐬
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Outdoor dining

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!
Heated Plunge Pool & Screened Lanai: 2BR/2BA Oasis Steps from North-End Beach
Enjoy cooking in this well-equipped kitchen with a central island, sink, and stainless steel appliances.

Heated Plunge Pool & Screened Lanai: 2BR/2BA Oasis Steps from North-End Beach

10.0 out of 10, Exceptional, (1)
"The house was perfect for us, very comfortable and clean. NIce size bedrooms and confy beds we really enjoyed the stay.. The pool "Sitting Pool" is nice after a hot day at the beach"
Heated Plunge Pool & Screened Lanai: 2BR/2BA Oasis Steps from North-End Beach
Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!
Relax in this serene beachfront retreat with a comfortable bed, a nightstand, and a sliding door leading to a balcony with ocean views.

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!
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Classic design with a large painting, console table, and bench in a well-appointed room.

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

9.8 out of 10, Exceptional, (87)
"Excellent place for relaxing beach vacation"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views
Enjoy the serene ocean views from this balcony with a pool and access to the sandy 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
Adorable Beach cottage just steps Bean Point beach!
Relax by the pool surrounded by lush greenery and a comfortable seating area.

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 €802
includes taxes & fees
22 Jul - 23 Jul
Adorable Beach cottage just steps Bean Point beach!
Bayfront home with Private dock near Famous Bridge Street - Seaside Serenity
Stroll along the serene waterfront pier, taking in the tranquil atmosphere.

Bayfront home with Private dock near Famous Bridge Street - Seaside Serenity

10.0 out of 10, Exceptional, (4)
"We have stayed here multiple times and it is exactly as described and what we want. Great location and views. Close to restaurants, beaches and free shuttle."
Bayfront home with Private dock near Famous Bridge Street - Seaside Serenity
Right across the street from Beach! Incredible Views! - Coquina Breeze
Guests can enjoy a wide, open beach with turquoise waters and a clear view of the sky.

Right across the street from Beach! Incredible Views! - Coquina Breeze

9.4 out of 10, Exceptional, (3)
"Pretty nice house, clean, feel like home"
The price is €660
includes taxes & fees
25 Jul - 26 Jul
Right across the street from Beach! Incredible Views! - Coquina Breeze
SUGAR REEF "B" One Minute Walk to the Beach!
Enjoy a peaceful beach experience with calm seas and scenic views.

SUGAR REEF "B" One Minute Walk to the Beach!

10.0 out of 10, Exceptional, (130)
"We had a great time at Sugar Reef B. Very comfortable space for two! Excellent response from Laura if we had questions. Would stay here again!"
SUGAR REEF "B" One Minute Walk to the Beach!
Walk-up suite with on-site pool, private deck, full kitchen - walk to beach
Relax by the pool surrounded by lush greenery and palm trees, featuring a rectangular pool with lounge chairs and a decorative statue.

Walk-up suite with on-site pool, private deck, full kitchen - walk to beach

9.2 out of 10, Wonderful, (12)
"Loved the quick access to the beach and pool area, perfect little spot"
Walk-up suite with on-site pool, private deck, full kitchen - walk to beach
Anna Maria Beach Condo 1/1
Situated on the beach, this wooden structure features a series of arches and a checkered roof.

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (180)
"Nice place very roomy easy check in very close to beach and restaurants"
The price is €328
includes taxes & fees
21 Jul - 22 Jul
Anna Maria Beach Condo 1/1
#201 Sand Piper: 2B / 2B
Staircase leads to an upper level with a large window offering a view of the outdoors.

#201 Sand Piper: 2B / 2B

10.0 out of 10, Exceptional, (8)
"The property was clean and so cute! Right across the street from the beach. Great view. The pool was great also. "
#201 Sand Piper: 2B / 2B
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
Enjoy cooking in this well-equipped kitchen with appliances, a central island, and ample counter space.

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

2.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful stay ! Our family loved it ! "
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!
Escape to Anna Maria Island!
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, microwave, and coffee maker.

Escape to Anna Maria Island!

10.0 out of 10, Exceptional, (117)
"Our stay was fantastic. Easy walking access to the beach, trolley and restaurants. "
Escape to Anna Maria Island!
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
Stunning coastal landscape with a pristine white sandy beach and lush vegetation.

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
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!
Relax by the serene pool, surrounded by lush greenery and a shaded seating area.

LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

9.4 out of 10, Exceptional, (128)
"Our family had a wonderful time here for spring break. The pool was especially nice because the wading area was perfect for our 2 year old to play with water toys. And we had a very short walk to the beach at Bean Point, which was lovely. The beds were very comfortable and the kitchen was supplied with everything we needed. We rented an electric golf cart, which was easily charged at the outdoor outlet. Also, we appreciated the pack and play, the beach wagon, beach chairs, and pool toys....
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!
Elevator SPACIOUS Luxury Home Fab Reviews, Heated Pool/Spa, 3 min walk to beach!
Relax by the rectangular pool surrounded by a deck and lush greenery, complete with lounge chairs and a covered seating area.

Elevator SPACIOUS Luxury Home Fab Reviews, Heated Pool/Spa, 3 min walk to beach!

10.0 out of 10, Exceptional, (159)
"We had a blast at this great spot. This house has everything you need!"
Elevator SPACIOUS Luxury Home Fab Reviews, Heated Pool/Spa, 3 min walk to beach!
Near Bean Point!! Short stays available! Heated Pool
Stunning pool surrounded by lush greenery and palm trees, set amidst a variety of architectural styles.

Near Bean Point!! Short stays available! Heated Pool

9.6 out of 10, Exceptional, (48)
"This place is wonderful!!! Just a few steps from the beach, the location is excellent! The house was extremely clean and had everything we needed! Everything was perfect and we even had an incredible barbecue. We had a great time!!! Thank you for welcoming us so well. We will definitely be back."
Near Bean Point!! Short stays available! Heated Pool
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!
Enjoy stunning ocean views from the balcony, where you can relax in the outdoor seating area.

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

9.6 out of 10, Exceptional, (9)
"Had an amazing stay. Beautiful property and close to beach. Property manager was very responsive and answered messages very quickly. Would stay here again in the future! "
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!
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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