COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals
✕

Anna Maria Island Waterfront Vacation Rentals, Beach Rentals & More - 112 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

112 Vacation rentals

Filters applied: Waterfront

(5)

1 / 26

Bradenton Beach Apartment

  • 1
  • 5
  • min stay varies
  • Air conditioning

Responds fast! Avg. 3 hours 48 minutes

$338.00

Excellent (5 reviews)

Book

from $338.00 / night

Book

(3)

1 / 31

Bradenton Beach Cottage

  • 2
  • 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 3 hours 48 minutes

“My husband and I spent the weekend in this cottage to celebrate his milestone birthday. We found it to be very comfortable and welcoming. I especially love the sunroom for my morning coffee and yoga. We were pleasantly surprised at how comfortable...”
- Review left on 11/23/2017

$189.00

Very Good (3 reviews)

Book

from $189.00 / night

Book

(25)

1 / 21

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 9 minutes

“Songbird is a little slice of heaven with everything we needed to have a comfortable stay. We stayed for one week. Joel, the owner, is very thoughtful, and accommodating, and he makes it known that he is there for you if you need him. Which is so...”
- Review left on 05/20/2017

$126.00

Excellent (25 reviews)

Book

from $126.00 / night

Book
1 / 19

Bradenton Beach Cottage

  • 1
  • 3
  • 2 nights min
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 3 hours 48 minutes

$229.00

Book

from $229.00 / night

Book

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

Responds fast! Avg. 3 hours 48 minutes

$304.00

Excellent (1 reviews)

Book

from $304.00 / night

Book

(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 5 minutes

Certificate of Excellence

“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$344.00

Excellent (23 reviews)

Book

from $344.00 / night

Book

(7)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$229.00

Very Good (7 reviews)

Book

from $229.00 / night

Book

(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 48 minutes

$383.00

Excellent (2 reviews)

Book

from $383.00 / night

Book

(2)

1 / 31

Anna Maria Island Cottage

  • 1
  • 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Car not necessary

Responds fast! Avg. 3 hours 48 minutes

$189.00

Very Good (2 reviews)

Book

from $189.00 / night

Book
1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$655.00

Book

from $655.00 / night

Book

(3)

1 / 36

Bradenton Beach Cottage

  • 2
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 48 minutes

$189.00

Excellent (3 reviews)

Book

from $189.00 / night

Book

(21)

1 / 17

Holmes Beach Townhouse

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$184.00

Very Good (21 reviews)

Book

from $184.00 / night

Book

(5)

1 / 27

Holmes Beach Condo

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning
“My Husband ,Son & I had a wonderful time at the Condo,it was clean ,comfortable & near the beach ,shops & the bus stops.I could not ask for anything better ,will be looking to rent again in the future”
- Review left on 09/01/2015

$126.00

Excellent (5 reviews)

Book

from $126.00 / night

Book
1 / 26

Bradenton Beach Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$262.00

Book

from $262.00 / night

Book
1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$429.00

Book

from $429.00 / night

Book
1 / 32

Anna Maria Island House

  • 1
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

$345.00

Book

from $345.00 / night

Book
1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$373.00

Book

from $373.00 / night

Book
1 / 34

Bradenton Beach House

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning

$299.00

Book

from $299.00 / night

Book
1 / 34

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$410.00

Book

from $410.00 / night

Book
1 / 31

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$273.00

Book

from $273.00 / night

Book
1 / 34

Bradenton Beach House

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$291.00

Book

from $291.00 / night

Book
1 / 33

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$223.00

Book

from $223.00 / night

Book
1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$375.00

Book

from $375.00 / night

Book
1 / 34

Anna Maria Island House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$650.00

Book

from $650.00 / night

Book
1 / 35

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$345.00

Book

from $345.00 / night

Book
1 / 35

Bradenton Beach House

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$381.00

Book

from $381.00 / night

Book
1 / 35

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$377.00

Book

from $377.00 / night

Book
1 / 35

Bradenton Beach Condo

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning

$260.00

Book

from $260.00 / night

Book
1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

Book

from $258.00 / night

Book
1 / 24

Holmes Beach Condo

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$365.00

Book

from $365.00 / night

Book
1 / 33

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$294.00

Book

from $294.00 / night

Book
1 / 24

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$410.00

Book

from $410.00 / night

Book
1 / 32

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$280.00

Book

from $280.00 / night

Book
1 / 32

Bradenton Beach House

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$350.00

Book

from $350.00 / night

Book

Your search has been expanded 19 miles to include more rentals

1 / 36

St. Petersburg House - 17.9 miles away

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,374.00

Book

from $1,374.00 / night

Book

(12)

1 / 23

Bradenton House - 16.9 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$279.00

Excellent (12 reviews)

Book

from $279.00 / night

Book
1 / 33

Bradenton House - 8.4 miles away

  • 3
  • 6
  • 2 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$138.00

Book

from $138.00 / night

Book

(1)

1 / 26

Sarasota Cottage - 16.8 miles away

  • 1
  • 3
  • 7 nights min
  • Air conditioning
  • Private garden

$116.00

Excellent (1 reviews)

Book

from $116.00 / night

Book

(1)

1 / 13

Lakewood Ranch House - 19 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

Average (1 reviews)

Book

from $279.00 / night

Book
1 / 15

Bradenton House - 9.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$457.00

Book

from $457.00 / night

Book