Search 105,200+ Vacation Rentals

Anna Maria 2-bedroom Vacation Rentals, Beach Rentals & More - 150 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

150 Vacation rentals

Filters applied: 2+ Bedrooms

(23)

1 / 49

Anna Maria House

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 37 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$201.00

Very Good (23 reviews)

Book

from $201.00 / night

(1)

1 / 21

Anna Maria House

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$573.00

Excellent (1 reviews)

Book

from $573.00 / night

1 / 51

Anna Maria Apartment

  • 5
  • 12
  • 4 nights min
  • Child friendly

$799.00

Book

from $799.00 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$573.00

Book

from $573.00 / night

(2)

1 / 47

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 9 minutes

$383.00

Excellent (2 reviews)

Book

from $383.00 / night

1 / 55

Anna Maria House

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$687.00

Book

from $687.00 / night

Your search has been expanded 19.8 miles to include more rentals

(2)

1 / 27

Madeira Beach Condo - 19 miles away

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

$152.00

Excellent (2 reviews)

Book

from $152.00 / night

(1)

1 / 66

Redington Beach House - 19.8 miles away

  • 5
  • 14
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$343.00

Excellent (1 reviews)

Book

from $343.00 / night

(4)

1 / 19

Bradenton Villa - 17.4 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$180.00

Excellent (4 reviews)

Inquire

from $180.00 / night

1 / 13

Lakewood Ranch House - 18.9 miles away

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

$279.00

Book

from $279.00 / night

(25)

1 / 24

Bradenton House - 14.3 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 38 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (25 reviews)

Book

from $150.00 / night

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$155.00

Book

from $155.00 / night

(2)

1 / 16

Sarasota Condo - 12.6 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$114.00

Very Good (2 reviews)

Book

from $114.00 / night

(4)

1 / 14

Madeira Beach Condo - 19.3 miles away

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Enjoyed the vacation. Rented 2 condos for family of10 for the week of July 4. Nice rooms, great beach, and amazing 4th of July fireworks on the beach from 8:30 until nearly 11:00. never seen fireworks like that before...”
- Review left on 07/18/2015

$148.00

Very Good (4 reviews)

Book

from $148.00 / night

(60)

1 / 28

Treasure Island Condo - 15.3 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“First and foremost, Nick was easily the most wonderful owner we have ever dealt with. He was quick to get back with us on any email and very pleasant. The condo is perfectly located on the beach, minutes from everything and walking distance to Caddy'...”
- Review left on 04/05/2017

$141.00

Excellent (60 reviews)

Inquire

from $141.00 / night

(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“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

$164.00

Very Good (11 reviews)

Book

from $164.00 / night

(1)

1 / 33

Anna Maria Island Villa - 4.9 miles away

  • 2
  • 3
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 9 minutes

$201.00

Excellent (1 reviews)

Book

from $201.00 / night

1 / 27

Madeira Beach Condo - 19 miles away

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

$164.00

Book

from $164.00 / night

(24)

1 / 30

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Gulf front condo in Madeira Beach; location/view is outstanding and condo was fully equipped. Convenient to restaurants, shopping and attractions. Only two complaints were the carpet in unit was dirty, stained and worn and needed to be cleaned or...”
- Review left on 11/28/2016

$229.00

Very Good (24 reviews)

Book

from $229.00 / night

(20)

1 / 108

St. Petersburg Condo - 12.4 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“We had stayed all around Florida , but Never had a view like this, water everywhere, from all the windows. When you see the pictures they are gorgeous but in real life Wow. I think this is one of the best condo's we have stayed in. The owners are...”
- Review left on 05/30/2017

$229.00

Excellent (20 reviews)

Book

from $229.00 / night

(3)

1 / 16

Bradenton House - 17.1 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$144.00

Excellent (3 reviews)

Book

from $144.00 / night

(27)

1 / 11

Bradenton House - 17.2 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The home was a great place for our group to stay. It was clean and well maintained. The location was ideal, close to golf courses and shopping and many good restaurants. We would definitely stay there again. The owner, Larry was very good to work...”
- Review left on 02/01/2017

$210.00

Excellent (27 reviews)

Inquire

from $210.00 / night

(1)

1 / 18

Madeira Beach Condo - 19 miles away

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

$152.00

Excellent (1 reviews)

Book

from $152.00 / night

(9)

1 / 15

Madeira Beach Townhouse - 18.1 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
“I have stayed at Townhouse 343 for several years and have recommended it to several of my friends and co-workers. Neither I, nor any of my friends have ever been disappointed. The owners are hospitable and think of every detail to make your stay...”
- Review left on 10/08/2016

$118.00

Very Good (9 reviews)

Book

from $118.00 / night

(3)

1 / 38

Redington Beach Manor house - 19.7 miles away

  • 5
  • 12
  • 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

1 / 14

Madeira Beach Condo - 18.3 miles away

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

$172.00

Book

from $172.00 / night

1 / 42

Madeira Beach Apartment - 18 miles away

  • 2
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$229.00

Book

from $229.00 / night

(6)

1 / 40

Bradenton House - 17.5 miles away

  • 3
  • 6
  • 30 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
“As soon as I unlocked the door to this property and looked in, I turned to my wife and said, "you're definitely going to be impressed" and needless to say she was!The home was by far the best we ever rented and I would have even rated it higher than...”
- Review left on 06/17/2016

$137.00

Excellent (6 reviews)

Inquire

from $137.00 / night

1 / 17

Madeira Beach Condo - 18.3 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly

Responds fast! Avg. 3 hours 30 minutes

$218.00

Book

from $218.00 / night

(7)

1 / 12

St. Petersburg Condo - 13 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Pet friendly
“We thoroughly enjoyed our stay in this beautiful condo overlooking Boca Ciega Bay.. Very clean, comfortable home, what a nice view of the bay with dolphins regularly swimming by! The owner, Ken, was stellar to deal with, all our needs were totally...”
- Review left on 05/21/2016

Inquire for Rates

Excellent (7 reviews)

Inquire

Pricing unknown

1 / 12

Madeira Beach Apartment - 18 miles away

  • 2
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$315.00

Book

from $315.00 / night

1 / 21

Madeira Beach Condo - 19.1 miles away

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

$264.00

Book

from $264.00 / night

1 / 15

Madeira Beach Condo - 19.4 miles away

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$287.00

Book

from $287.00 / night

(1)

1 / 30

St. Petersburg Condo - 12.4 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$72.00

Excellent (1 reviews)

Inquire

from $72.00 / night

1 / 34

St. Petersburg Condo - 12.3 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$82.00

Inquire

from $82.00 / night

(1)

1 / 33

St. Petersburg Apartment - 12.4 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$72.00

Excellent (1 reviews)

Inquire

from $72.00 / night

1 / 32

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

Inquire

from $72.00 / night

(1)

1 / 38

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$82.00

Excellent (1 reviews)

Inquire

from $82.00 / night

(4)

1 / 32

St. Petersburg Apartment - 12.3 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$86.00

Excellent (4 reviews)

Inquire

from $86.00 / night

1 / 32

St. Petersburg Apartment - 12.4 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

Inquire

from $72.00 / night