Vacation Rentals
44 properties available
Enchanting, seashell-pink, Gulf-front 3br/2ba vacation getaway on Anna Maria Island. This freshly renovated 1,032 sq ft, Key West-style single-family home was originally built in 1940 and still glows with all the charm of a quintessential “old Florida” beach cottage. Yet, it’s been beautifully renovated inside and out; transformed into a sleek, sty
AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace
3BR 2BR House
$275.00 - $903.00 / per night
3
bedrooms
2
baths
6
guests
4.9
(21)
Welcome to the heart of Holmes Beach, just four blocks (a five-minute stroll) to the beach! Blue Bella is a comfortable, contemporary 1,822 sf Anna Maria ranch home with five bedrooms and three baths. The home sleeps up to ten guests. Enjoy a pool, a shaded, fenced back patio with a grill, alfresco dining, and a fire pit circled by Adirondack chair
Anna Maria Island Blue Bella Bliss - Private Heated Pool
Holmes Beach
$250.00 - $1,005.00 / per night
5
bedrooms
3
baths
10
guests
This sun-drenched 2br/2ba beach cottage centrally located by Holmes Beach in the heart of Anna Maria has been described as one of the “prettiest vacation homes on the island.” This authentic 1947 beach bungalow has been completely (and splendidly!) renovated with raised ceilings, travertine floors, and showers, granite countertops in the kitchens a
Anna Maria Island Edgewater Bungalow
2BR 2BR House
$180.00 - $741.00 / per night
2
bedrooms
2
baths
6
guests
4.8
(8)
This Direct Gulf Front, first floor, vacation house located on Bradenton Beach offers the perfect location on Anna Maria Island to enjoy a relaxing tropical setting. The views of the Gulf of Mexico from the kitchen, dining and living room are truly breathtaking. Sliding glass doors from the living room lead to the private porch where you can watch
Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR
1BD 1BR
$175.00 - $567.00 / per night
1
bedrooms
1
baths
2
guests
4.8
(9)
ACCOMMODATIONS:The Beach Palms 7A is a gorgeous 2 bedroom, 2 bathroom first floor condo that sleeps 6, a boat and fishing dock, heated pool, and 2 parking spots. The north balcony is a private balcony directly over looking the heated pool and it accessed by 2 sets of sliding glass doors from the living room. The white sand beaches are 125 yards to
Anna Maria Island Beach Palms 7A
2 BR 2BA Condo
$129.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
4.9
(27)
The Beach Bay Breeze condo is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that leads right out onto the pier, famous for strolling, fishing and eating and the restaurant at the end of the pier.Bed Configura
Anna Maria Island Beach Bay Breeze
2 BR 2BA Condo
$120.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
5
(8)
The Anna Maria Island Beach Sands #101 overlooks the Gulf of Mexico is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that leads right out onto the pier, famous for strolling, fishing and eating and the restau
Anna Maria Island Beach Sands 101
2 BR 2BA Condo
$182.00 - $717.00 / per night
2
bedrooms
2
baths
6
guests
5
(60)
Bed Configuration:- Primary Bedroom - One King Bed-Second Bedroom - One Queen Bed - One Twin Bed(Sleeps Five)*With our continued desire to provide a superior guest experience we offer all our guests a professional linen service which includes freshly laundered sheets, pillow cases, bath towels, hand towels, beach towels, wash cloths, dish cloths an
Anna Maria Island Bay Watch Bungalow
2 BR 2BA Condo
$153.00 - $581.00 / per night
2
bedrooms
2
baths
5
guests
4.8
(23)
The coastal morning is serene; white sand beaches glow gold in the sunrise. The aquamarine Gulf of Mexico sparkles with crystals of sunlight. Dolphins breach along the horizon. Relax on your screened-in lanai and sip your coffee, or fresh-squeezed citrus juice, as palm fronds dance in the salt breeze. THIS is the vacation you’ve been dreaming of.Di
Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From Every Window
2 BR 2BA Condo
$123.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
Discover your perfect getaway at Runaway Bay, an award-winning condominium development of 186 one- and two-bedroom units at the south end of picturesque Anna Maria Island. Located between where the Gulf of Mexico meets Anna Maria Island’s west beaches and the island’s eastern side of Anna Maria Sound and Palma Sola Bay, this prime location allows g
Runaway Tropical Waves-Pet Friendly
2 BR 2BA Condo
$115.00 - $430.00 / per night
2
bedrooms
2
baths
4
guests
Anna Maria Island Beach Palace offers incredible views in every direction because it’s situated in the best location on the entire island! The island is only 150 yards wide where this 3-story condo is located. The Gulf of Mexico is merely 75 yards to the west, and Florida’s Intracoastal Waterway is 75 yards to the east.Relax on the 3rd-floor, ceram
Anna Maria Island Beach Palace
4BR 3BA House
$375.00 - $1,527.00 / per night
4
bedrooms
3
baths
8
guests
4.9
(65)
Look in almost any direction, and there are views of the bay, the gulf, and even downtown Sarasota. Steps away from the white sand beaches of Gulf of Mexico, this 2 bedroom/2 bathroom condo at Baywatch is located high up in the treetops near the shore of Anna Maria Sound. Renters can enjoy the peek-a-boo bay views from the oversized open-aired balc
Anna Maria Island Beach Palms 8B
2 BR 2BA Condo
$120.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
5
(20)
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