373 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Anna Maria Island Long Term Vacation Rentals(373)

373 Results
$1,500 - $1,950
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(61)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
4 - 7 night min stay
(27)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 28 night min stay
(20)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 28 night min stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(58)
$450 - $700
per night
4 - 6 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 6 night min stay
(18)
$450 - $700
per night
4 - 6 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
4 - 6 night min stay
(25)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(19)
$1,800 - $2,000
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(19)
$165 - $235
per night
4 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
4 night min stay
(7)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night min stay
(6)
$800 - $1,500
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 20 night min stay
(16)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
7 night min stay
(5)
$159 - $169
per night
6 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
6 night min stay
(3)
$2,030 - $3,080
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
7 night min stay
(24)
$113 - $120
per night
3 - 30 night min stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 30 night min stay
(14)
$4,000
per week
7 night min stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
7 night min stay
(16)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
(12)
$399 - $499
per night
3 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
3 night min stay
(5)
$2,100 - $3,080
per week
6 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
6 - 7 night min stay
(17)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
1 Review
$142 - $303
per night
6 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night min stay
(16)
$142 - $303
per night
6 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night min stay
(31)
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
1 Review
$200 - $393
per night
5 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 7 night min stay
(18)
 View map Map
Advertisement
 

Recent Anna Maria Island Reviews

Amazing place to stay!

5 of 5
First time in Anna Maria and it was an amazing time. The location is perfect, and the condo is a block away from the beach. Super clean and cute place to stay. Perfect for families, girls trip, or a romantic getaway. I will stay there in a heartbeat on my next vacation to Anna Maria! Dan is a great guy to work with as well!
  • Submitted: Apr 14, 2015
  • Stayed: Jul 2014

Exceeded our Expectations

5 of 5
We enjoyed our month stay at The Little Mermaid tremendously. This little cottage is equipped with everything you need. Both the King bed and Queen sleeper sofa are very comfortable. The sheets and towels were also very nice. Having the additional half bathroom was a real bonus. It was a such a pleasure to have our own washer and dryer too. We love this location on the island because it's just across the street from the beach. Betty, the owner, is delightful and always available if you need her, plus full of information about the island.
  • Submitted: Apr 12, 2015
  • Stayed: Mar 2015

Very comfortable with great access to the beach.

4 of 5
We had a great month of March @ Beach & Bay Retreat. It is a comfortable place with the porch being a great place for relaxing and eating al fresco. One living/family room couch has seen better days & is too soft and needs replacing, but overall we would definitely return if given the chance. Easy access to the beach and a free trolley stop. Owner is very accommodating & checks to see if everything is going well with your stay.
  • Submitted: Apr 7, 2015
  • Stayed: Mar 2015