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 — photo 6

Barefoot by the Bay at Bayside Bungalow — photo 7

Barefoot by the Bay at Bayside Bungalow — photo 8

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 — photo 6

Bay Breezes at Bayside Bungalow — photo 7

Bay Breezes at Bayside Bungalow — photo 8

Bay Breezes at Bayside Bungalow

2 bedrooms · 2 beds · 1 bathroom

From$200/ 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 — photo 6

Bay Vista at Bayside Bungalow — photo 7

Bay Vista at Bayside Bungalow — photo 8

Bay Vista at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$282/ night

Blissful Bay at Bayside Bungalow — photo 1

Blissful Bay at Bayside Bungalow — photo 2

Blissful Bay at Bayside Bungalow — photo 3

Blissful Bay at Bayside Bungalow — photo 4

Blissful Bay at Bayside Bungalow — photo 5

Blissful Bay at Bayside Bungalow — photo 6

Blissful Bay at Bayside Bungalow — photo 7

Blissful Bay at Bayside Bungalow — photo 8

Blissful Bay at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$275/ 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 — photo 6

Bayside Cutie at Bayside Bungalow — photo 7

Bayside Cutie at Bayside Bungalow — photo 8

Bayside Cutie at Bayside Bungalow

1 bedroom · 1 bed · 1 bathroom

From$175/ night

Turtle Trax — photo 1

Turtle Trax — photo 2

Turtle Trax — photo 3

Turtle Trax — photo 4

Turtle Trax — photo 5

Turtle Trax — photo 6

Turtle Trax — photo 7

Turtle Trax — photo 8

Turtle Trax

2 bedrooms · 2 beds · 1 bathroom

From$175/ 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 — photo 6

A Place in Paradise Unit A — photo 7

A Place in Paradise Unit A — photo 8

A Place in Paradise Unit A

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Social Nest — photo 1

Social Nest — photo 2

Social Nest — photo 3

Social Nest — photo 4

Social Nest — photo 5

Social Nest — photo 6

Social Nest — photo 7

Social Nest — photo 8

Social Nest

3 bedrooms · 3 beds · 2 bathrooms

From$187/ 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 — photo 6

Pink Palm Bungalow — photo 7

Pink Palm Bungalow — photo 8

Pink Palm Bungalow

3 bedrooms · 4 beds · 2 bathrooms

From$245/ night

Magnolia Shores — photo 1

Magnolia Shores — photo 2

Magnolia Shores — photo 3

Magnolia Shores — photo 4

Magnolia Shores — photo 5

Magnolia Shores — photo 6

Magnolia Shores — photo 7

Magnolia Shores — photo 8

Magnolia Shores

2 bedrooms · 5 beds · 1 bathroom

From$211/ 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 — photo 6

Beach You To It — photo 7

Beach You To It — photo 8

Beach You To It

3 bedrooms · 4 beds · 2 bathrooms

From$285/ night

Absolutely Anna — photo 1

Absolutely Anna — photo 2

Absolutely Anna — photo 3

Absolutely Anna — photo 4

Absolutely Anna — photo 5

Absolutely Anna — photo 6

Absolutely Anna — photo 7

Absolutely Anna — photo 8

Absolutely Anna

2 bedrooms · 2 beds · 2 bathrooms

From$231/ night

Shore's Nice — photo 1

Shore's Nice — photo 2

Shore's Nice — photo 3

Shore's Nice — photo 4

Shore's Nice — photo 5

Shore's Nice — photo 6

Shore's Nice — photo 7

Shore's Nice — photo 8

Shore's Nice

2 bedrooms · 2 beds · 2 bathrooms

From$225/ night

Covey Cottage — photo 1

Covey Cottage — photo 2

Covey Cottage — photo 3

Covey Cottage — photo 4

Covey Cottage — photo 5

Covey Cottage — photo 6

Covey Cottage — photo 7

Covey Cottage — photo 8

Covey Cottage

3 bedrooms · 3 beds · 3.5 bathrooms

From$189/ night

Chardonnay Shores — photo 1

Chardonnay Shores — photo 2

Chardonnay Shores — photo 3

Chardonnay Shores — photo 4

Chardonnay Shores — photo 5

Chardonnay Shores — photo 6

Chardonnay Shores — photo 7

Chardonnay Shores — photo 8

Chardonnay Shores

3 bedrooms · 3 beds · 2 bathrooms

From$295/ night

Tiny Tides — photo 1

Tiny Tides — photo 2

Tiny Tides — photo 3

Tiny Tides — photo 4

Tiny Tides — photo 5

Tiny Tides — photo 6

Tiny Tides — photo 7

Tiny Tides — photo 8

Tiny Tides

2 bedrooms · 2 beds · 1 bathroom

From$100/ night

Beachcombers — photo 1

Beachcombers — photo 2

Beachcombers — photo 3

Beachcombers — photo 4

Beachcombers — photo 5

Beachcombers — photo 6

Beachcombers — photo 7

Beachcombers — photo 8

Beachcombers

3 bedrooms · 5 beds · 2 bathrooms

From$200/ 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 — photo 6

Anna Maria Guest House 212 — photo 7

Anna Maria Guest House 212 — photo 8

Anna Maria Guest House 212

3 bedrooms · 6 beds · 2 bathrooms

From$195/ night

Coconuts Beachfront #112 — photo 1

Coconuts Beachfront #112 — photo 2

Coconuts Beachfront #112 — photo 3

Coconuts Beachfront #112 — photo 4

Coconuts Beachfront #112 — photo 5

Coconuts Beachfront #112 — photo 6

Coconuts Beachfront #112 — photo 7

Coconuts Beachfront #112 — photo 8

Coconuts Beachfront #112

Holmes Beach, FL

1 bedroom · 1 bed · 1 bathroom

From$226/ night

A Wave From It All — photo 1

A Wave From It All — photo 2

A Wave From It All — photo 3

A Wave From It All — photo 4

A Wave From It All — photo 5

A Wave From It All — photo 6

A Wave From It All — photo 7

A Wave From It All — photo 8

A Wave From It All

5 bedrooms · 8 beds · 6.5 bathrooms

From$1,036/ night

Casa Allegria — photo 1

Casa Allegria — photo 2

Casa Allegria — photo 3

Casa Allegria — photo 4

Casa Allegria — photo 5

Casa Allegria — photo 6

Casa Allegria — photo 7

Casa Allegria — photo 8

Casa Allegria

3 bedrooms · 4 beds · 2 bathrooms

From$250/ night

Anna Maria Guest House 317 — photo 1

Anna Maria Guest House 317 — photo 2

Anna Maria Guest House 317 — photo 3

Anna Maria Guest House 317 — photo 4

Anna Maria Guest House 317 — photo 5

Anna Maria Guest House 317 — photo 6

Anna Maria Guest House 317 — photo 7

Anna Maria Guest House 317 — photo 8

Anna Maria Guest House 317

3 bedrooms · 4 beds · 2 bathrooms

From$225/ night

Gulf Shore Cottage — photo 1

Gulf Shore Cottage — photo 2

Gulf Shore Cottage — photo 3

Gulf Shore Cottage — photo 4

Gulf Shore Cottage — photo 5

Gulf Shore Cottage — photo 6

Gulf Shore Cottage — photo 7

Gulf Shore Cottage — photo 8

Gulf Shore Cottage

4 bedrooms · 5 beds · 2 bathrooms

From$290/ night

Little Pink Houses — photo 1

Little Pink Houses — photo 2

Little Pink Houses — photo 3

Little Pink Houses — photo 4

Little Pink Houses — photo 5

Little Pink Houses — photo 6

Little Pink Houses — photo 7

Little Pink Houses — photo 8

Little Pink Houses

3 bedrooms · 5 beds · 3 bathrooms

From$206/ 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 — photo 6

Barefoot by the Bay at Bayside Bungalow — photo 7

Barefoot by the Bay at Bayside Bungalow — photo 8

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 — photo 6

Bay Breezes at Bayside Bungalow — photo 7

Bay Breezes at Bayside Bungalow — photo 8

Bay Breezes at Bayside Bungalow

2 bedrooms · 2 beds · 1 bathroom

From$200/ 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 — photo 6

Bay Vista at Bayside Bungalow — photo 7

Bay Vista at Bayside Bungalow — photo 8

Bay Vista at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$282/ night

Blissful Bay at Bayside Bungalow — photo 1

Blissful Bay at Bayside Bungalow — photo 2

Blissful Bay at Bayside Bungalow — photo 3

Blissful Bay at Bayside Bungalow — photo 4

Blissful Bay at Bayside Bungalow — photo 5

Blissful Bay at Bayside Bungalow — photo 6

Blissful Bay at Bayside Bungalow — photo 7

Blissful Bay at Bayside Bungalow — photo 8

Blissful Bay at Bayside Bungalow

3 bedrooms · 3 beds · 2 bathrooms

From$275/ 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 — photo 6

Bayside Cutie at Bayside Bungalow — photo 7

Bayside Cutie at Bayside Bungalow — photo 8

Bayside Cutie at Bayside Bungalow

1 bedroom · 1 bed · 1 bathroom

From$175/ night

Turtle Trax — photo 1

Turtle Trax — photo 2

Turtle Trax — photo 3

Turtle Trax — photo 4

Turtle Trax — photo 5

Turtle Trax — photo 6

Turtle Trax — photo 7

Turtle Trax — photo 8

Turtle Trax

2 bedrooms · 2 beds · 1 bathroom

From$175/ 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 — photo 6

A Place in Paradise Unit A — photo 7

A Place in Paradise Unit A — photo 8

A Place in Paradise Unit A

2 bedrooms · 3 beds · 2 bathrooms

From$109/ night

Social Nest — photo 1

Social Nest — photo 2

Social Nest — photo 3

Social Nest — photo 4

Social Nest — photo 5

Social Nest — photo 6

Social Nest — photo 7

Social Nest — photo 8

Social Nest

3 bedrooms · 3 beds · 2 bathrooms

From$187/ 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 — photo 6

Pink Palm Bungalow — photo 7

Pink Palm Bungalow — photo 8

Pink Palm Bungalow

3 bedrooms · 4 beds · 2 bathrooms

From$245/ night

Magnolia Shores — photo 1

Magnolia Shores — photo 2

Magnolia Shores — photo 3

Magnolia Shores — photo 4

Magnolia Shores — photo 5

Magnolia Shores — photo 6

Magnolia Shores — photo 7

Magnolia Shores — photo 8

Magnolia Shores

2 bedrooms · 5 beds · 1 bathroom

From$211/ 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 — photo 6

Beach You To It — photo 7

Beach You To It — photo 8

Beach You To It

3 bedrooms · 4 beds · 2 bathrooms

From$285/ night

Absolutely Anna — photo 1

Absolutely Anna — photo 2

Absolutely Anna — photo 3

Absolutely Anna — photo 4

Absolutely Anna — photo 5

Absolutely Anna — photo 6

Absolutely Anna — photo 7

Absolutely Anna — photo 8

Absolutely Anna

2 bedrooms · 2 beds · 2 bathrooms

From$231/ night

Shore's Nice — photo 1

Shore's Nice — photo 2

Shore's Nice — photo 3

Shore's Nice — photo 4

Shore's Nice — photo 5

Shore's Nice — photo 6

Shore's Nice — photo 7

Shore's Nice — photo 8

Shore's Nice

2 bedrooms · 2 beds · 2 bathrooms

From$225/ night

Covey Cottage — photo 1

Covey Cottage — photo 2

Covey Cottage — photo 3

Covey Cottage — photo 4

Covey Cottage — photo 5

Covey Cottage — photo 6

Covey Cottage — photo 7

Covey Cottage — photo 8

Covey Cottage

3 bedrooms · 3 beds · 3.5 bathrooms

From$189/ night

Chardonnay Shores — photo 1

Chardonnay Shores — photo 2

Chardonnay Shores — photo 3

Chardonnay Shores — photo 4

Chardonnay Shores — photo 5

Chardonnay Shores — photo 6

Chardonnay Shores — photo 7

Chardonnay Shores — photo 8

Chardonnay Shores

3 bedrooms · 3 beds · 2 bathrooms

From$295/ night

Tiny Tides — photo 1

Tiny Tides — photo 2

Tiny Tides — photo 3

Tiny Tides — photo 4

Tiny Tides — photo 5

Tiny Tides — photo 6

Tiny Tides — photo 7

Tiny Tides — photo 8

Tiny Tides

2 bedrooms · 2 beds · 1 bathroom

From$100/ night

Beachcombers — photo 1

Beachcombers — photo 2

Beachcombers — photo 3

Beachcombers — photo 4

Beachcombers — photo 5

Beachcombers — photo 6

Beachcombers — photo 7

Beachcombers — photo 8

Beachcombers

3 bedrooms · 5 beds · 2 bathrooms

From$200/ 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 — photo 6

Anna Maria Guest House 212 — photo 7

Anna Maria Guest House 212 — photo 8

Anna Maria Guest House 212

3 bedrooms · 6 beds · 2 bathrooms

From$195/ night

Coconuts Beachfront #112 — photo 1

Coconuts Beachfront #112 — photo 2

Coconuts Beachfront #112 — photo 3

Coconuts Beachfront #112 — photo 4

Coconuts Beachfront #112 — photo 5

Coconuts Beachfront #112 — photo 6

Coconuts Beachfront #112 — photo 7

Coconuts Beachfront #112 — photo 8

Coconuts Beachfront #112

Holmes Beach, FL

1 bedroom · 1 bed · 1 bathroom

From$226/ night

A Wave From It All — photo 1

A Wave From It All — photo 2

A Wave From It All — photo 3

A Wave From It All — photo 4

A Wave From It All — photo 5

A Wave From It All — photo 6

A Wave From It All — photo 7

A Wave From It All — photo 8

A Wave From It All

5 bedrooms · 8 beds · 6.5 bathrooms

From$1,036/ night

Casa Allegria — photo 1

Casa Allegria — photo 2

Casa Allegria — photo 3

Casa Allegria — photo 4

Casa Allegria — photo 5

Casa Allegria — photo 6

Casa Allegria — photo 7

Casa Allegria — photo 8

Casa Allegria

3 bedrooms · 4 beds · 2 bathrooms

From$250/ night

Anna Maria Guest House 317 — photo 1

Anna Maria Guest House 317 — photo 2

Anna Maria Guest House 317 — photo 3

Anna Maria Guest House 317 — photo 4

Anna Maria Guest House 317 — photo 5

Anna Maria Guest House 317 — photo 6

Anna Maria Guest House 317 — photo 7

Anna Maria Guest House 317 — photo 8

Anna Maria Guest House 317

3 bedrooms · 4 beds · 2 bathrooms

From$225/ night

Gulf Shore Cottage — photo 1

Gulf Shore Cottage — photo 2

Gulf Shore Cottage — photo 3

Gulf Shore Cottage — photo 4

Gulf Shore Cottage — photo 5

Gulf Shore Cottage — photo 6

Gulf Shore Cottage — photo 7

Gulf Shore Cottage — photo 8

Gulf Shore Cottage

4 bedrooms · 5 beds · 2 bathrooms

From$290/ night

Little Pink Houses — photo 1

Little Pink Houses — photo 2

Little Pink Houses — photo 3

Little Pink Houses — photo 4

Little Pink Houses — photo 5

Little Pink Houses — photo 6

Little Pink Houses — photo 7

Little Pink Houses — photo 8

Little Pink Houses

3 bedrooms · 5 beds · 3 bathrooms

From$206/ night