Anna Maria Island Accommodations — Vacation Rentals

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169 of 169 listings

Barefoot by the Bay at Bayside Bungalow — photo 1

Barefoot by the Bay at Bayside Bungalow — photo 2

Barefoot by the Bay at Bayside Bungalow — photo 3

Barefoot by the Bay at Bayside Bungalow — photo 4

Barefoot by the Bay at Bayside Bungalow — photo 5

Barefoot by the Bay at Bayside Bungalow

1 bedroom · 1 bed · 2 bathrooms

From$175/ night

Bay Breezes at Bayside Bungalow — photo 1

Bay Breezes at Bayside Bungalow — photo 2

Bay Breezes at Bayside Bungalow — photo 3

Bay Breezes at Bayside Bungalow — photo 4

Bay Breezes at Bayside Bungalow — photo 5

Bay Breezes at Bayside Bungalow

2 bedrooms · 2 beds · 1 bathroom

From$200/ night

Salt Life — photo 1

Salt Life — photo 2

Salt Life — photo 3

Salt Life — photo 4

Salt Life — photo 5

Salt Life

Bradenton Beach, FL

5 bedrooms · 5 beds · 5.5 bathrooms

From$1,016/ night

Bayside Cutie at Bayside Bungalow — photo 1

Bayside Cutie at Bayside Bungalow — photo 2

Bayside Cutie at Bayside Bungalow — photo 3

Bayside Cutie at Bayside Bungalow — photo 4

Bayside Cutie at Bayside Bungalow — photo 5

Bayside Cutie at Bayside Bungalow

1 bedroom · 1 bed · 1 bathroom

From$175/ night

Walking on Sunshine — photo 1

Walking on Sunshine — photo 2

Walking on Sunshine — photo 3

Walking on Sunshine — photo 4

Walking on Sunshine — photo 5

Walking on Sunshine

Holmes Beach, FL

3 bedrooms · 3 beds · 3 bathrooms

From$225/ night

Just Beachy — photo 1

Just Beachy — photo 2

Just Beachy — photo 3

Just Beachy — photo 4

Just Beachy — photo 5

Just Beachy

Holmes Beach, FL

6 bedrooms · 6 beds · 4.5 bathrooms

From$1,175/ night

Turtle Crawl — photo 1

Turtle Crawl — photo 2

Turtle Crawl — photo 3

Turtle Crawl — photo 4

Turtle Crawl — photo 5

Turtle Crawl

2 bedrooms · 2 beds · 2 bathrooms

From$180/ night

Bay Vista at Bayside Bungalow — photo 1

Bay Vista at Bayside Bungalow — photo 2

Bay Vista at Bayside Bungalow — photo 3

Bay Vista at Bayside Bungalow — photo 4

Bay Vista at Bayside Bungalow — photo 5

Bay Vista at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$282/ night

Magnolia Shores — photo 1

Magnolia Shores — photo 2

Magnolia Shores — photo 3

Magnolia Shores — photo 4

Magnolia Shores — photo 5

Magnolia Shores

2 bedrooms · 5 beds · 1 bathroom

From$211/ night

Social Nest — photo 1

Social Nest — photo 2

Social Nest — photo 3

Social Nest — photo 4

Social Nest — photo 5

Social Nest

3 bedrooms · 3 beds · 2 bathrooms

From$187/ night

Orange Crush — photo 1

Orange Crush — photo 2

Orange Crush — photo 3

Orange Crush — photo 4

Orange Crush — photo 5

Orange Crush

Holmes Beach, FL

3 bedrooms · 3 beds · 2 bathrooms

From$154/ night

A Place in Paradise Unit B — photo 1

A Place in Paradise Unit B — photo 2

A Place in Paradise Unit B — photo 3

A Place in Paradise Unit B — photo 4

A Place in Paradise Unit B — photo 5

A Place in Paradise Unit B

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Beach You To It — photo 1

Beach You To It — photo 2

Beach You To It — photo 3

Beach You To It — photo 4

Beach You To It — photo 5

Beach You To It

3 bedrooms · 4 beds · 2 bathrooms

From$285/ night

A Place in Paradise Unit A — photo 1

A Place in Paradise Unit A — photo 2

A Place in Paradise Unit A — photo 3

A Place in Paradise Unit A — photo 4

A Place in Paradise Unit A — photo 5

A Place in Paradise Unit A

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Our Place By The Sea — photo 1

Our Place By The Sea — photo 2

Our Place By The Sea — photo 3

Our Place By The Sea — photo 4

Our Place By The Sea — photo 5

Our Place By The Sea

3 bedrooms · 4 beds · 2.5 bathrooms

From$188/ night

Island Breeze — photo 1

Island Breeze — photo 2

Island Breeze — photo 3

Island Breeze — photo 4

Island Breeze — photo 5

Island Breeze

Holmes Beach, FL

3 bedrooms · 4 beds · 2 bathrooms

From$125/ night

Absolutely Anna — photo 1

Absolutely Anna — photo 2

Absolutely Anna — photo 3

Absolutely Anna — photo 4

Absolutely Anna — photo 5

Absolutely Anna

2 bedrooms · 2 beds · 2 bathrooms

From$231/ night

Captain Ron's Beach Pad — photo 1

Captain Ron's Beach Pad — photo 2

Captain Ron's Beach Pad — photo 3

Captain Ron's Beach Pad — photo 4

Captain Ron's Beach Pad — photo 5

Captain Ron's Beach Pad

Bradenton Beach, FL

2 bedrooms · 3 beds · 2 bathrooms

From$215/ night

Bo's Beach Bungalow — photo 1

Bo's Beach Bungalow — photo 2

Bo's Beach Bungalow — photo 3

Bo's Beach Bungalow — photo 4

Bo's Beach Bungalow — photo 5

Bo's Beach Bungalow

2 bedrooms · 3 beds · 1 bathroom

From$120/ night

Tiny Tides — photo 1

Tiny Tides — photo 2

Tiny Tides — photo 3

Tiny Tides — photo 4

Tiny Tides — photo 5

Tiny Tides

2 bedrooms · 2 beds · 1 bathroom

From$100/ night

Turtle Trax — photo 1

Turtle Trax — photo 2

Turtle Trax — photo 3

Turtle Trax — photo 4

Turtle Trax — photo 5

Turtle Trax

2 bedrooms · 2 beds · 1 bathroom

From$175/ night

Pink Palm Bungalow — photo 1

Pink Palm Bungalow — photo 2

Pink Palm Bungalow — photo 3

Pink Palm Bungalow — photo 4

Pink Palm Bungalow — photo 5

Pink Palm Bungalow

3 bedrooms · 4 beds · 2 bathrooms

From$245/ night

Anna Maria Guest House 212 — photo 1

Anna Maria Guest House 212 — photo 2

Anna Maria Guest House 212 — photo 3

Anna Maria Guest House 212 — photo 4

Anna Maria Guest House 212 — photo 5

Anna Maria Guest House 212

3 bedrooms · 6 beds · 2 bathrooms

From$195/ night

Chardonnay Shores — photo 1

Chardonnay Shores — photo 2

Chardonnay Shores — photo 3

Chardonnay Shores — photo 4

Chardonnay Shores — photo 5

Chardonnay Shores

3 bedrooms · 3 beds · 2 bathrooms

From$295/ night

Barefoot by the Bay at Bayside Bungalow — photo 1

Barefoot by the Bay at Bayside Bungalow — photo 2

Barefoot by the Bay at Bayside Bungalow — photo 3

Barefoot by the Bay at Bayside Bungalow — photo 4

Barefoot by the Bay at Bayside Bungalow — photo 5

Barefoot by the Bay at Bayside Bungalow

1 bedroom · 1 bed · 2 bathrooms

From$175/ night

Bay Breezes at Bayside Bungalow — photo 1

Bay Breezes at Bayside Bungalow — photo 2

Bay Breezes at Bayside Bungalow — photo 3

Bay Breezes at Bayside Bungalow — photo 4

Bay Breezes at Bayside Bungalow — photo 5

Bay Breezes at Bayside Bungalow

2 bedrooms · 2 beds · 1 bathroom

From$200/ night

Salt Life — photo 1

Salt Life — photo 2

Salt Life — photo 3

Salt Life — photo 4

Salt Life — photo 5

Salt Life

Bradenton Beach, FL

5 bedrooms · 5 beds · 5.5 bathrooms

From$1,016/ night

Bayside Cutie at Bayside Bungalow — photo 1

Bayside Cutie at Bayside Bungalow — photo 2

Bayside Cutie at Bayside Bungalow — photo 3

Bayside Cutie at Bayside Bungalow — photo 4

Bayside Cutie at Bayside Bungalow — photo 5

Bayside Cutie at Bayside Bungalow

1 bedroom · 1 bed · 1 bathroom

From$175/ night

Walking on Sunshine — photo 1

Walking on Sunshine — photo 2

Walking on Sunshine — photo 3

Walking on Sunshine — photo 4

Walking on Sunshine — photo 5

Walking on Sunshine

Holmes Beach, FL

3 bedrooms · 3 beds · 3 bathrooms

From$225/ night

Just Beachy — photo 1

Just Beachy — photo 2

Just Beachy — photo 3

Just Beachy — photo 4

Just Beachy — photo 5

Just Beachy

Holmes Beach, FL

6 bedrooms · 6 beds · 4.5 bathrooms

From$1,175/ night

Turtle Crawl — photo 1

Turtle Crawl — photo 2

Turtle Crawl — photo 3

Turtle Crawl — photo 4

Turtle Crawl — photo 5

Turtle Crawl

2 bedrooms · 2 beds · 2 bathrooms

From$180/ night

Bay Vista at Bayside Bungalow — photo 1

Bay Vista at Bayside Bungalow — photo 2

Bay Vista at Bayside Bungalow — photo 3

Bay Vista at Bayside Bungalow — photo 4

Bay Vista at Bayside Bungalow — photo 5

Bay Vista at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$282/ night

Magnolia Shores — photo 1

Magnolia Shores — photo 2

Magnolia Shores — photo 3

Magnolia Shores — photo 4

Magnolia Shores — photo 5

Magnolia Shores

2 bedrooms · 5 beds · 1 bathroom

From$211/ night

Social Nest — photo 1

Social Nest — photo 2

Social Nest — photo 3

Social Nest — photo 4

Social Nest — photo 5

Social Nest

3 bedrooms · 3 beds · 2 bathrooms

From$187/ night

Orange Crush — photo 1

Orange Crush — photo 2

Orange Crush — photo 3

Orange Crush — photo 4

Orange Crush — photo 5

Orange Crush

Holmes Beach, FL

3 bedrooms · 3 beds · 2 bathrooms

From$154/ night

A Place in Paradise Unit B — photo 1

A Place in Paradise Unit B — photo 2

A Place in Paradise Unit B — photo 3

A Place in Paradise Unit B — photo 4

A Place in Paradise Unit B — photo 5

A Place in Paradise Unit B

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Beach You To It — photo 1

Beach You To It — photo 2

Beach You To It — photo 3

Beach You To It — photo 4

Beach You To It — photo 5

Beach You To It

3 bedrooms · 4 beds · 2 bathrooms

From$285/ night

A Place in Paradise Unit A — photo 1

A Place in Paradise Unit A — photo 2

A Place in Paradise Unit A — photo 3

A Place in Paradise Unit A — photo 4

A Place in Paradise Unit A — photo 5

A Place in Paradise Unit A

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Our Place By The Sea — photo 1

Our Place By The Sea — photo 2

Our Place By The Sea — photo 3

Our Place By The Sea — photo 4

Our Place By The Sea — photo 5

Our Place By The Sea

3 bedrooms · 4 beds · 2.5 bathrooms

From$188/ night

Island Breeze — photo 1

Island Breeze — photo 2

Island Breeze — photo 3

Island Breeze — photo 4

Island Breeze — photo 5

Island Breeze

Holmes Beach, FL

3 bedrooms · 4 beds · 2 bathrooms

From$125/ night

Absolutely Anna — photo 1

Absolutely Anna — photo 2

Absolutely Anna — photo 3

Absolutely Anna — photo 4

Absolutely Anna — photo 5

Absolutely Anna

2 bedrooms · 2 beds · 2 bathrooms

From$231/ night

Captain Ron's Beach Pad — photo 1

Captain Ron's Beach Pad — photo 2

Captain Ron's Beach Pad — photo 3

Captain Ron's Beach Pad — photo 4

Captain Ron's Beach Pad — photo 5

Captain Ron's Beach Pad

Bradenton Beach, FL

2 bedrooms · 3 beds · 2 bathrooms

From$215/ night

Bo's Beach Bungalow — photo 1

Bo's Beach Bungalow — photo 2

Bo's Beach Bungalow — photo 3

Bo's Beach Bungalow — photo 4

Bo's Beach Bungalow — photo 5

Bo's Beach Bungalow

2 bedrooms · 3 beds · 1 bathroom

From$120/ night

Tiny Tides — photo 1

Tiny Tides — photo 2

Tiny Tides — photo 3

Tiny Tides — photo 4

Tiny Tides — photo 5

Tiny Tides

2 bedrooms · 2 beds · 1 bathroom

From$100/ night

Turtle Trax — photo 1

Turtle Trax — photo 2

Turtle Trax — photo 3

Turtle Trax — photo 4

Turtle Trax — photo 5

Turtle Trax

2 bedrooms · 2 beds · 1 bathroom

From$175/ night

Pink Palm Bungalow — photo 1

Pink Palm Bungalow — photo 2

Pink Palm Bungalow — photo 3

Pink Palm Bungalow — photo 4

Pink Palm Bungalow — photo 5

Pink Palm Bungalow

3 bedrooms · 4 beds · 2 bathrooms

From$245/ night

Anna Maria Guest House 212 — photo 1

Anna Maria Guest House 212 — photo 2

Anna Maria Guest House 212 — photo 3

Anna Maria Guest House 212 — photo 4

Anna Maria Guest House 212 — photo 5

Anna Maria Guest House 212

3 bedrooms · 6 beds · 2 bathrooms

From$195/ night

Chardonnay Shores — photo 1

Chardonnay Shores — photo 2

Chardonnay Shores — photo 3

Chardonnay Shores — photo 4

Chardonnay Shores — photo 5

Chardonnay Shores

3 bedrooms · 3 beds · 2 bathrooms

From$295/ night