Search Vacation Homes in Anna Maria

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

Charming Bungalow with Fabulous Location and Private Pool!

9.8 out of 10, Exceptional, (155)
"The location is just a block from the beach and lots of unique restaurants. The pool area is great!"
Charming Bungalow with Fabulous Location and Private Pool!

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

9.8 out of 10, Exceptional, (87)
"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-

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

9.4 out of 10, Exceptional, (125)
"Amazing time. Wonderful set up, CLEAN, GREAT pool and hot tub. Great host to communicate with as well. 3 min walk to the beach. Sand toys plenty of pool towels and linens. Very accommodating, would recommend anyone to stay here! "
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!

8 Palms: Gorgeous heated pool and lounge area, with putt-putt!

10.0 out of 10, Exceptional, (13)
"We really enjoyed the pool and the backyard. Bed were comfy too!"
8 Palms: Gorgeous heated pool and lounge area, with putt-putt!

Desirable North-End Gem on Canal with Dock, Heated Pool. Clean and Spacious.

9.8 out of 10, Exceptional, (110)
"Plenty of space, very clean, excellent location"
Desirable North-End Gem on Canal with Dock, Heated Pool. Clean and Spacious.

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

9.6 out of 10, Exceptional, (11)
"We were looking for relaxation and found it. This home is so adorable. Thepool was perfect for us. "
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

A Bay From It All: Private backyard oasis, steps to Bay, Bean Point

9.8 out of 10, Exceptional, (11)
"Enjoyed"
A Bay From It All: Private backyard oasis, steps to Bay, Bean Point

Holly Hideaway: Spacious 2 bed, heated pool, screened lanai, 5-mins to beach

Holly Hideaway: Spacious 2 bed, heated pool, screened lanai, 5-mins to beach

Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals

9.6 out of 10, Exceptional, (19)
"Great property. Close to beach, nice pool, lots of toys games for kids, clean, etc. Highly recommend "
Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals

Golf Cart, Simpatico by SeaBreeze Vacation

9.4 out of 10, Exceptional, (16)
"A great place for our group of 6. Absolutely loved the pool and being on the canal!"
Golf Cart, Simpatico by SeaBreeze Vacation

Bridgeview: Bay front with sweeping views, sleeps 12!

9.8 out of 10, Exceptional, (39)
"Beautiful home! There was plenty of room for gathering as a family to celebrate my birthday and Mother’s Day. The large table was my favorite part of house…a large round table that can sit up to 12 people. (10 chairs at the table) The Eagle’s nest was also a hit with my family. It was so peaceful and it was a great place to watch the sunrise and the sunset. Plenty of bedrooms and bathrooms…everyone had their own space. The house is well decorated and it was so nice that they provided plenty of...
Bridgeview: Bay front with sweeping views, sleeps 12!

Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat

10.0 out of 10, Exceptional, (148)
"We really enjoyed our week at Angels Envy. House is beautifully decorated and the kitchen is very well supplied and made life easy for us. With the beautiful view we ate most of our meals in We fell in love with this little house "
Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat

CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...

9.0 out of 10, Wonderful, (42)
"I be back again! "
CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley,...

Vitamin Sea managed by Beach Retreats FL Anna Maria Island

9.6 out of 10, Exceptional, (42)
"We had a wonderful stay at Vitamin Sea! Great location and beautiful house. "
Vitamin Sea managed by Beach Retreats FL Anna Maria Island

Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals

8.8 out of 10, Excellent, (40)
"Lovely stay"
Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals

Summer 2025 Special: FREE bikes & paddleboard!

10.0 out of 10, Exceptional, (3)
"A lovely stay I highly recommend it. The house, the view, the location, and the town, all so nice. Our family and friends loved it too!!!! You really had a vision when you built this place and you made it a vacation that will always stay with us."
Summer 2025 Special: FREE bikes & paddleboard!

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

10.0 out of 10, Exceptional, (225)
"This was a beautiful house with an amazing location! We loved our stay!"
Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches

9.6 out of 10, Exceptional, (84)
"My family and I loved the house and of course Anna Maria island was the prettiest place we’ve been so far!!!!"
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches

The Wee Cottage | House in Anna Maria

8.4 out of 10, Very Good, (15)
"Easy and close beach access. Location nearby all amenities and necessities. Did not see that the a/c units were window units, the bedroom unit is AMAZING, however the main room unit was mediocre. The Wee Cottage is adorable!!!"
The Wee Cottage | House in Anna Maria

Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants

10.0 out of 10, Exceptional, (18)
"The property was very clean and the location was great."
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
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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