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 2-bedroom Vacation Rentals, Beach Rentals & More - 79 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

79 Vacation rentals

Filters applied: 2+ Bedrooms

(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 16 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

(28)

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

$218.00

Excellent (28 reviews)

Book

from $218.00 / night

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

Responds fast! Avg. 3 hours 16 minutes

$304.00

Excellent (1 reviews)

Book

from $304.00 / night

(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

Travelers’ Choice award

“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

$487.00

Excellent (23 reviews)

Book

from $487.00 / night

(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

$230.00

Very Good (7 reviews)

Book

from $230.00 / night

(2)

1 / 72

Anna Maria House

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

Responds fast! Avg. 3 hours 16 minutes

$418.00

Excellent (2 reviews)

Book

from $418.00 / night

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

(3)

1 / 36

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 16 minutes

$189.00

Excellent (3 reviews)

Book

from $189.00 / night

(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

(5)

1 / 24

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

1 / 26

Bradenton Beach Villa

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

$262.00

Book

from $262.00 / night

1 / 34

Anna Maria Island House

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

$429.00

Book

from $429.00 / night

1 / 34

Anna Maria Island House

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

$373.00

Book

from $373.00 / night

1 / 34

Bradenton Beach House

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

$299.00

Book

from $299.00 / night

1 / 34

Anna Maria Island House

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

$410.00

Book

from $410.00 / night

1 / 31

Anna Maria Island House

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

$273.00

Book

from $273.00 / night

1 / 34

Bradenton Beach House

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

$291.00

Book

from $291.00 / night

1 / 33

Anna Maria Island House

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

$224.00

Book

from $224.00 / night

1 / 34

Anna Maria Island House

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

$375.00

Book

from $375.00 / night

1 / 34

Anna Maria Island House

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

$650.00

Book

from $650.00 / night

1 / 35

Anna Maria Island House

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

$345.00

Book

from $345.00 / night

1 / 35

Bradenton Beach House

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

$381.00

Book

from $381.00 / night

1 / 35

Anna Maria Island House

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

$377.00

Book

from $377.00 / night

1 / 35

Bradenton Beach Condo

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

$260.00

Book

from $260.00 / night

1 / 34

Anna Maria Island House

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

$258.00

Book

from $258.00 / night

1 / 33

Anna Maria Island House

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

$294.00

Book

from $294.00 / night

1 / 24

Anna Maria Island House

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

$410.00

Book

from $410.00 / night

1 / 32

Anna Maria Island House

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

$280.00

Book

from $280.00 / night

1 / 32

Bradenton Beach House

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

$350.00

Book

from $350.00 / night

Your search has been expanded 19.7 miles to include more rentals

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

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

(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$107.00

Very Good (1 reviews)

Book

from $107.00 / night

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

1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,145.00

Book

from $1,145.00 / night

1 / 14

Madeira Beach Condo - 18.4 miles away

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

$230.00

Book

from $230.00 / night

(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 48 minutes

“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$115.00

Excellent (3 reviews)

Book

from $115.00 / night

(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile radius...”
- Review left on 04/07/2017

$189.00

Very Good (11 reviews)

Book

from $189.00 / night

(5)

1 / 29

Bradenton Condo - 9.1 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 26 minutes

$138.00

Very Good (5 reviews)

Book

from $138.00 / night

(1)

1 / 13

Lakewood Ranch House - 19 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Air conditioning

$230.00

Average (1 reviews)

Book

from $230.00 / night

(3)

1 / 43

Redington Beach Manor house - 19.7 miles away

  • 5
  • 13
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This home was amazing. We brought three generations and had plenty of space--both for together times and when we wanted privacy! Three teenage girls enjoyed the privacy of the garage suite. We called it the bachelorette pad! The pool and patio area...”
- Review left on 10/22/2017

$1,145.00

Excellent (3 reviews)

Book

from $1,145.00 / night