Anna Maria Vacation Rental Getaways


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  • Beach Front
  • Golf on site
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Sort by: Type BR/BA/Sleeps Price

Magnolia Duplex A

Anna Maria
Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedr...
Home 2 / 1 / 4

*
Online booking available

$165 - $305
Per Night

$1155 - $2135
Per Week

Sweet Retreat Cottage

Anna Maria
Cozy enough for honeymooners but room for a family of eight, you’re not going to feel any guilt abou...
Cottage 3 / 2 / 8

*
Online booking available

$300 - $600
Per Night

$2100 - $4200
Per Week

Sea's the Day

Anna Maria
The various shades of blue throughout Sea's the Day make this a  water lover's dream vacation cottag...
Cottage 2 / 2 / 6

*
Online booking available

$225 - $380
Per Night

$1575 - $2660
Per Week

Bikini Bottom

Anna Maria
Bikini Bottom on Periwinkle is just a short walk -- only nine houses -- to the beautiful, pristine b...
Home 3 / 2 / 6

*
Online booking available

$285 - $470
Per Night

$1995 - $3290
Per Week

Gorgeous Periwinkle Cottage

Anna Maria
Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. ...
Cottage 3 / 2 / 6

*
Online booking available

$290 - $425
Per Night

$2030 - $2975
Per Week

Rest a Shore

Anna Maria
There is getting away from it all and there’s completely removing yourself from reality. Experience ...
Home 4 / 3.5 / 8

*
Online booking available

$465 - $1005
Per Night

$3255 - $7035
Per Week

Anna Maria's Finest

Anna Maria
When you stay at vacation rental home “Anna Maria’s Finest” you’ll experience the luxurious side of ...
Home 3 / 3 / 8

*
Online booking available

$365 - $585
Per Night

$2555 - $4095
Per Week

Maple Cottage

Anna Maria
Time spent on Anna Maria Island should be savored. We islanders move through our day with a slower, ...
Home 3 / 2 / 8

*
Online booking available

$225 - $365
Per Night

$1575 - $2555
Per Week

Blue Heron Beach House

Anna Maria
4 Bedroom, 2 Bath (sleeps 8) - "Blue Heron Beach House" - 117 Peppertree Lane in Anna Maria.  Welco...
Cottage 4 / 2 / 8

*
Online booking available

$320 - $600
Per Night

$2240 - $4200
Per Week

Periwinkle Home with Dock Access 208

Anna Maria
Living at the beach is like living anywhere else except it’s better in almost every way imaginable. ...
Home 3 / 2.5 / 8

*
Online booking available

$285 - $495
Per Night

$1995 - $3465
Per Week

Paradise Pointe

Anna Maria
Paradise Pointe, located in the quiet north end of beautiful Anna Maria awaits the vacationer in you...
Home 3 / 2 / 8

*
Online booking available

$385 - $585
Per Night

$2695 - $4095
Per Week

HoneyWood House

Anna Maria
Living at the beach is like living anywhere else except its better in almost every way imaginable! E...
Home 3 / 4 / 8

*
Online booking available

$350 - $595
Per Night

$2450 - $4165
Per Week

A Sassy Seahorse

Anna Maria
The special "North End" vacation rental is immaculately clean and whimsically decorated, professiona...
Home 2 / 2 / 6

*
Online booking available

$285 - $575
Per Night

$1995 - $4025
Per Week

Blue Waters

Anna Maria
  Located at the prestigious north end of Anna Maria, Blue Waters is brand new  to the rental progr...
Home 4 / 4 / 8

*
Online booking available

$530 - $1090
Per Night

$3710 - $7665
Per Week

619 Rose - Dream Maker

Anna Maria
Absolutely stunning in every way! This ultimate luxury beach vacation rental home is for relaxing wi...
Home 3 / 3.5 / 6

*
Online booking available

$485 - $600
Per Night

$3395 - $4200
Per Week

Mangrove Cottage

Anna Maria
Staying at Mangrove Cottage, known to some as simply “Mangrove Cottage”, is less about vacationing a...
Cottage 2 / 2 / 5

*
Online booking available

$225 - $380
Per Night

$1575 - $2660
Per Week

Shoreline Terrace

Anna Maria
 4 Bedroom, 2.5 Bath (sleeps 8) - "Shoreline Terrace" - 901 North Shore Drive, Anna Maria Anna Mari...
Cottage 4 / 2.5 / 10

*
Online booking available

$420 - $840
Per Night

$2940 - $5880
Per Week

LaRaya-801 Jacaranda

Anna Maria
Welcome to 801 Jacaranda Road located at the north end of beautiful Anna Maria Island, less than 2 b...
Home 3 / 2 / 6

*
Online booking available

$300 - $600
Per Night

$2100 - $4200
Per Week

Sugar Plum Hideaway East

Anna Maria
(3) Bedroom, (2) Bath (Sleeps 6) – “Sugar Plum Hideaway East”- 114 Mangrove East in Anna Maria You’...
Home 3 / 2 / 6

*
Online booking available

$285 - $480
Per Night

$1995 - $3360
Per Week

Cayman Bay 505 Magnolia

Anna Maria
A unique and truly luxurious vacation experience is waiting for you at Anna Maria vacation rental “C...
Home 4 / 4 / 8

*
Online booking available

$465 - $910
Per Night

$3255 - $6370
Per Week

Beach Pearl 212 Archer Way

Anna Maria
Just a short stroll from Gulf of Mexico beaches, Anna Maria vacation rental “Beach Pearl” offers a l...
Home 3 / 2 / 6

*
Online booking available

$335 - $500
Per Night

$2345 - $3500
Per Week

Sea 'Esta

Anna Maria
Spend your holiday in Sea ‘Esta and enjoy sweet dreams, suntans, and a short walk to the beach. Slee...
Home 2 / 2 / 5

*
Online booking available

$185 - $380
Per Night

$1295 - $2660
Per Week

Magnolia Duplex B

Anna Maria
People choose Anna Maria Island for their family vacations because we have a slower, simpler way of ...
Home 2 / 1 / 6

*
Online booking available

$180 - $345
Per Night

$1295 - $2415
Per Week

My Sisters Beach House

Anna Maria
Immaculate, stunning and spacious multi-level holiday island rental. (5) Bedroom, (4) Bathroom, acco...
Home 5 / 4 / 10

*
Online booking available

$590 - $1300
Per Night

$4130 - $9100
Per Week

Living The Dream

Anna Maria
"Living The Dream" is a spacious 2,650 sq. ft. luxurious private vacation rental home with an attach...
Home 4 / 3 / 8

*
Online booking available

$480 - $685
Per Night

$3360 - $4795
Per Week

 

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