Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Cottages
Hotels
Homes
Lodges
Studios
Townhomes
Villas
Barns
Boats
Cabins
Castles
Chalets
Estates
Farmhouses
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Anna Maria Island Vacation Home Rentals with Air Conditioning(444)

444 Results
$186 - $250
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(61)
$400 - $650
per night
4 - 5 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 5 night minimum stay
(14)
$257 - $486
per night
5 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
5 - 7 night minimum stay
(39)
$1,000 - $2,650
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
7 night minimum stay
(14)
$400 - $700
per night
4 - 5 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
4 - 5 night minimum stay
(16)
$195 - $270
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(13)
$1,000 - $1,600
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(11)
$1,595 - $1,950
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(11)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
4 - 7 night minimum stay
(9)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 16
7 night minimum stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(31)
$215 - $329
per night
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 5 night minimum stay
(5)
$1,820 - $2,730
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
7 night minimum stay
(17)
$1,435 - $2,100
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(20)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
$1,600 - $2,000
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(19)
$1,600 - $2,000
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 - 14 night minimum stay
(35)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(6)
$250 - $295
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(4)
$139 - $199
per night
3 - 30 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 30 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(16)
$236 - $343
per night
5 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 7 night minimum stay
(16)
$1,820 - $2,730
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(11)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
4 night minimum stay
(7)
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(8)
 

Recent Anna Maria Island Reviews

Adorable!

5 of 5
We just had a fabulous time on Anna Maria at Cozy Cottage! The cottage was just the right size - not too small, not too big. Everything we needed was provided, which makes packing easy. The pool area was simply the best feature overall. We met our friends from Albuquerque and they loved the pool! We definitely want to book again next year and stay longer. The owners were very helpful with restaurant suggestions and keeping in touch with us throughout our stay. I highly recommend The Cozy Cottage to anyone looking for a nice, quiet, clean, well maintained, and "close to the beach" cottage.
  • Submitted: Nov 1, 2014
  • Stayed: Oct 2014

PERFECT LOCATION, VERY CLEAN AND ROOMY

5 of 5
We had an amazing time at the Toasty Coconut. We had four adults and a 9-month old, and the house included anything we could possibly need; beach chairs, tons of towels, pack n' play, a cooler, beach umbrella. I honestly can't think of anything that we needed that wasn't there when we arrived. The pool was clean and much larger than most private pools at other rentals. Staying on the island itself was amazing, no traffic and the beach was not near as busy as any public beach I have ever been on. I can't wait to go back and we will definitely stay at the Toasty Coconut again. Also, Ammey was very quick to respond to any questions I had and my deposit was returned in full within two days of checking out. I see why many of the reviewers have been staying there for multiple years, it truly is a place you will want to return to.
  • Submitted: Oct 15, 2014
  • Stayed: Sep 2014

Great house and great location

5 of 5
We really enjoyed this house, its amenities, its location, and the owners' thoughtfulness and responsiveness. The backyard was great! We loved the pool and the fact that we could dock our boat. The beach and restaurants are walking distance and this is a great section of the island. We can't wait to go back. Thanks Ramona.
  • Submitted: Sep 5, 2014
  • Stayed: Aug 2014