152 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Anna Maria House Rentals(152)

152 Results
$1,400 - $3,000
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
(6)
$193 - $250
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(65)
$193 - $250
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night min stay
(54)
  • 5 BR,
  • 2 BA,
  • Sleeps 13
7 night min stay
(20)
$2,520 - $6,500
per week
7 night min stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 16
7 night min stay
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(16)
$1,800 - $2,000
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(19)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night min stay
(6)
$1,900 - $2,800
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(5)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
7 night min stay
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(32)
$2,030 - $3,080
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
7 night min stay
(25)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
(4)
$2,100 - $3,080
per week
6 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
6 - 7 night min stay
(17)
$4,000
per week
7 night min stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
7 night min stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(11)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
(4)
$229 - $393
per night
5 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 7 night min stay
(18)
$1,000 - $1,900
per week
7 night min stay
  • 2 BR,
  • 3 BA,
  • Sleeps 4
7 night min stay
(20)
$1,633 - $2,400
per week
7 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 - 30 night min stay
(25)
$2,600 - $3,200
per week
7 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 16
7 night min stay
(7)
$450 - $700
per night
4 - 6 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 6 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night min stay
(7)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(4)
$200 - $279
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(15)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night min stay
 View map Map
Advertisement
 

Recent Anna Maria Reviews

Wonderful Vacation!

5 of 5
My husband and I absolutely loved our stay. The porch area was great when we wanted to get out of the sun. The pool area was beautiful, relaxing and very refreshing. We loved the convenience of the dock to walk right out to the boat in the morning, and especially the fact that you do not have a boat lift blocking a majority of the dock. The location is great, and we loved that it was within walking distance to one of our favorite places, Slims. We hope to be back within the year. Thank you again for sharing your beautiful home with us!
  • Submitted: May 21, 2015
  • Stayed: May 2015

Excellent!

5 of 5
This property was very clean and well decorated. The linens and furnishings felt like they were purchased for the owner and not renters. Everything you needed was provided and even some of the basic spices were there which was a pleasant surprise. The backyard is very private with a gorgeous pool which we enjoyed immensely. The fact that this was a single story home was especially convenient since both of us had some lower back issues on this visit. Ramona is great to work with and having a lockbox on the door is so much nicer than having to pick up and drop off keys. We have rented on Anna Maria previously and usually stayed further north and closer walking distance to the activities on Pine, but the free trolley stops just a block away to take you all over the island. Overall, I'd say Diamond Surf is one of the nicest homes we've rented and would definitely recommend it to others.
  • Submitted: Apr 10, 2015
  • Stayed: Mar 2015

Heart of my heart

5 of 5
The Cozy Cottage captured my heart the very first time my spouse and I stayed here. The surroundings are so calm, peaceful and PRIVATE you find yourself never wanting to leave. We feel so lucky to have found the Cottage as my spouse looked at hundreds of other rentals but something drew me to the Cottage and we have both never regretted our decision.
  • Submitted: Jan 5, 2015
  • Stayed: Jan 2015