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Vacation Homes in Anna Maria Island

Our top choices for Anna Maria Island vacation homes

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

10.0 out of 10, Exceptional, (1)
"The house is beautiful!! Plenty of room for a family, and plenty to do!The owner was readily available through messages and the phone if we had any questions. It was an easy process, and an excellent experience!!!I highly recommend this house if you just feel like hanging out, or exploring Anna Maria, it’s a beautiful location!!And don’t forget to go down the slide!! "
The price is ¥82,118
¥219,336 total
includes taxes & fees
Oct 13 - Oct 14
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

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

9.8 out of 10, Exceptional, (90)
"Excellent place for relaxing beach vacation"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

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

10.0 out of 10, Exceptional, (134)
"The beach is just a block away and it is one of the best sections of this island!"
SUGAR REEF "B" One Minute Walk to the Beach!

SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (186)
"Bay view was nice "
The price is ¥56,595
¥126,984 total
includes taxes & fees
Sep 21 - Sep 22
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

2 BR 2 Full BA on Anna Maria Island just steps to Beach!

10.0 out of 10, Exceptional, (170)
"Just steps away from the beach, the property has everything you need for the beach, chairs, umbrellas, etc "
2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Gulf-views inside home, Pool, duplex, SUP+Kayak+Firepit+Patio+Crows Nest+Grill

10.0 out of 10, Exceptional, (190)
"First trip as a family of 4. House was great we had the upstairs unit. Short walk to beach. Im really tall so was ducking fans but we enjoyed it. We would go again. We go to the AMI area every year and this was another enjoyable stay."
Gulf-views inside home, Pool, duplex, SUP+Kayak+Firepit+Patio+Crows Nest+Grill

HUGE Fall discounts on this canal front home! Putt putt, paddle boards,kayaks

10.0 out of 10, Exceptional, (1)
" “We had a wonderful experience. Everything was very clean, comfortable, and had everything we needed to enjoy quality time with the family. We created unforgettable memories and truly felt at home. The host was very attentive, always available with quick responses and ready to help with anything we needed. We would definitely love to come back!”"
HUGE Fall discounts on this canal front home! Putt putt, paddle boards,kayaks

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

9.4 out of 10, Exceptional, (133)
"This house worked perfectly for our annual girls trip! Beautifully remodeled - had everything we needed! Great pool/hot tub! We enjoyed ourselves!!"
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

2nd-floor duplex near beach with heated pool, grill, balcony, & W/D

8.8 out of 10, Excellent, (29)
"Nice place"
2nd-floor duplex near beach with heated pool, grill, balcony, & W/D

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (186)
"Excellent location, great condo, good local restaurants. "
The price is ¥18,495
¥48,444 total
includes taxes & fees
Sep 24 - Sep 25
Anna Maria Beach Condo 1/1

Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!

10.0 out of 10, Exceptional, (1)
"Excellent stay"
Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!

Rooftop Deck - Island Oasis by SeaBreeze Vacation

9.6 out of 10, Exceptional, (9)
"This was a great place for our family to stay for the weekend. Several of the rooms had ensuites, giving our adult children privacy. So close to the beach, and the rooftop was amazing. "
Rooftop Deck - Island Oasis by SeaBreeze Vacation

Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations

9.6 out of 10, Exceptional, (12)
"Our family had one of the best vacations ever at this home. There was plenty of space, a bunch of games and the pool was great. Location was super close to the beach and walking distance to shopping and restaurants."
Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations

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

9.0 out of 10, Wonderful, (4)
"Well maintained propert and enjoyed our stay."
The price is ¥85,077
¥232,408 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

9.8 out of 10, Exceptional, (62)
"Perfect home for a family getaway "
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

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!

POOL and New Spa!! Private outdoor living with grill, tv, and refrigerator.

9.8 out of 10, Exceptional, (287)
"Great spot! Loved the pool and spa, and the outdoor area with the grill, TV, and fridge made it super easy to hang out and relax. Nice private setup—just a few small details could be improved, but overall a really good stay. "
POOL and New Spa!! Private outdoor living with grill, tv, and refrigerator.

Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!

10.0 out of 10, Exceptional, (134)
"We had a great time at this property. The set up is is perfect. They supply beach chairs, tent and a cart which made everything so easy with having 3 little kids. We would definitely come back. "
Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!

Escape to Anna Maria Island!

10.0 out of 10, Exceptional, (121)
"Wonderful stay as usual. Our 4th visit and we’ll keep coming back! "
Escape to Anna Maria Island!

2nd-floor duplex near the beach & bay with heated pool, grill, patio, W/D, AC

8.6 out of 10, Excellent, (19)
"This place was clean, comfortable and walking distance to beach shops and restaurants."
2nd-floor duplex near the beach & bay with heated pool, grill, patio, W/D, AC
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

Find out more about Anna Maria Island

Find out more about Anna Maria Island

Anna Maria Island Vacation Homes information

Number of reviews
1,620
Accommodation
1429 Vacation Homes
Lowest Price
¥48,444
Highest Price
¥232,408

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