Longboat Key
 
 
 

Longboat key streches for twelve miles between the waters of the Gulf of Mexico and Sarasota Bay.

 
 
 
Browse the listings near Longboat Key or filter by a nearby city from the list below.

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Featured Listings
 
House Of The Sun #306Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
House Of The Sun #409Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Siesta Dunes 8-205, 2nd Fl ...
2 bedroom Siesta Key Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
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House Of The Sun #306Gs

Sarasota
This Gulf Side unit is a beach paradise! This unit has new tile throughout the common areas, beige ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #409Gv

Sarasota
Ocean View
This Gulf View unit was recently renovated and has recently added a new sofa and chair. There is ti...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #402Gs

Sarasota
Virtual Tour This Gulf Side unit has new installed tile inthe common areas, with carpet in both bed...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #312Gv

Sarasota
Ocean View
This Gulf View unit has newly installed beige carpet throughout the common areas and a renovated mas...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #314Gv

Sarasota
Ocean View
This Gulf View unit has tile throughout common areas, 2 full size sofas and a leather recliner. The ...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Blue Dolphin Inn - Four units surrounding a tropical pool.

Anna Maria
Beach Access, Ocean nearby
The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria f...

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Condo 3 / 2 / 8

$1050 - $1470
Per Week

 
 

House Of The Sun #303Gs

Sarasota
Virtual Tour This Gulf Side unit has beige carpet throughout and is decorated with light shades of ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Starfish Beach Unit 4

Holmes Beach
When a starfish needs to get away from something and can’t, it will sometimes need to detach an arm....

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Cottage 2 / 2 / 6

Online Booking

$180 - $325
Per Night

$1295 - $2275
Per Week

 
 

Heron-Dolphi

Anna Maria
Beach Access
4 Bedroom, 2 Bath (sleeps 8) - "Heron-Dolphin" -706 Rose Street in Anna Maria. Anna Maria Island va...

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Home 4 / 2 / 8

Online Booking

$435 - $645
Per Night

$3045 - $4515
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’...

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Home 3 / 2 / 6

Online Booking

$285 - $480
Per Night

$1995 - $3360
Per Week

 
 

House Of The Sun #508Gv

Sarasota
Ocean View
Come stay in this beautiful, remodeled and redecorated ocean view apartment. It truly has that light...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Palm Isle 3203

Holmes Beach
The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Ann...

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Cottage 2 / 2 / 8

Online Booking

$200 - $340
Per Night

$1400 - $2380
Per Week

 
 

Coco Cabana Unit A

Holmes Beach
 3 Bedroom, 2 Bath (sleeps 8) - "Coco Cabana" - 309 A 58th Street, Holmes Beach Welcome to Coco Cab...

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Home 3 / 2 / 8

Online Booking

$285 - $400
Per Night

$1995 - $2800
Per Week

 
 

Casa Varadero

Holmes Beach
 Welcome to Casa Varadero a new ground level vacation rental home on Anna Maria Island in the quiet ...

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Home 4 / 3 / 8

Online Booking

$450 - $615
Per Night

$3150 - $4305
Per Week

 
 

Summer Breeze

Holmes Beach
The perfect place for a fun filled memorable vacation destination is waiting for you at the vacation...

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Home 4 / 3.5 / 10

Online Booking

$320 - $630
Per Night

$2240 - $4410
Per Week

 
 

Perico Bay Club Gorgeous Townhome

Bradenton
There is an additional $100 application fee that we be added and not included in online quote Peric...

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Home 2 / 2 / 6

Online Booking

$175 - $185
Per Night

$1225 - $1295
Per Week

 
 

My Sisters Beach House

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

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Home 5 / 4 / 10

Online Booking

$590 - $1300
Per Night

$4130 - $9100
Per Week

 
 

Ariel's By The Sea

Holmes Beach
“Ariel’s By the Sea” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacatio...

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Home 3 / 2 / 6

Online Booking

$290 - $425
Per Night

$2030 - $2975
Per Week

 
 

Bradenton Beach Club Unit 224

Bradenton Beach
Enjoy a week in tropical island luxury when you visit the beautiful “Bradenton Beach Club” unit 224!...

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Condo 2 / 2 / 6

Online Booking

$235 - $355
Per Night

$1645 - $2520
Per Week

 
 

House Of The Sun #501Gs

Sarasota
This beautiful unit was renovated in September 2010. There is porcelain tile in the common areas, li...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #509Gv

Sarasota
Ocean View
Virtual Tour This newly renovated Gulf View unit has new stainless steel appliances in the kitchen ...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #511Gf

Sarasota
Ocean Front
This nicely renovated Gulf Front unit is well equipped, and tastefully decorated with a tropical the...

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Condo 2 / 2 / 2

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
 

North Beach Village Unit 55

Holmes Beach
Recently updated, find the casual and relaxing Anna Maria Island paradise getaway you’ve dreamt of a...

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Home 3 / 2.5 / 6

Online Booking

$200 - $350
Per Night

$1400 - $2450
Per Week

 
 

Hidden Cove Unit 6

Holmes Beach
  Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedroo...

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Condo 2 / 2.5 / 4

Online Booking

$270 - $580
Per Night

$1890 - $4060
Per Week

 
 

Gulf Shores Unit 205

Holmes Beach
Welcome to Gulf Shores Condominiums! We more than know how to live a life of luxury, but simplicity ...

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Condo 3 / 2 / 8

Online Booking

$285 - $445
Per Night

$1995 - $3115
Per Week

 
           
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