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 #511Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 2
More Info
House Of The Sun #414Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Down by the Sea
3 bedroom Anna Maria Home Vacation Rental Home
3 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

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 #414Gf

Sarasota
Ocean Front
This Gulf Front condo recently underwent a renovation that boasts new granite counter-tops and cabin...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
May 1 - May 26   Book during this period today and save $50!
 

Florida Gulf side condo steps from fishing dock Mint clean!!

Bradenton Beach
Beach Access, Golf nearby
Our new ground level, 2 bedroom cottage (2 queen beds, 1 sleeper couch) is nothing like any other be...

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Condo 2 / 1 / 4

$100 - $300
Per Night

$700 - $1900
Per Week

 
 

House Of The Sun #305Gs

Sarasota
Virtual Tour This Gulf Side unit has a slight view of the water, but a beautiful view of the palm t...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #410Gv

Sarasota
Ocean View
This newly renovated two bedroom/two bath condo accommodates four comfortably and offers tropical dé...

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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

 
 

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

 
 

Fish House

Anna Maria
(3) Bedroom, (3) Bath (Sleeps 8) – “Fish House” – 231 Oak Avenue in Anna Maria. For the perfect Ann...

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Home 3 / 3 / 8

Online Booking

$365 - $585
Per Night

$2555 - $4095
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 ...

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Home 3 / 3 / 8

Online Booking

$365 - $585
Per Night

$2555 - $4095
Per Week

 
 

Casa Siesta, ground floor, 2 bedrooms, walk to Siesta Key...

Siesta Key
Casa Siesta makes fun in the sun so easy! The 2-bedroom, ground-floor condo is just a short walk fro...

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Condo 2 / 1 / 4

Online Booking

$71 - $242
Per Night

$495 - $1695
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

 
 

Windshore

Holmes Beach
  Windshore is an all new property that showcases designer quality furnishings and is fully equippe...

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Home 3 / 2 / 7

Online Booking

$285 - $415
Per Night

$1995 - $2905
Per Week

 
 

House Of The Sun #311Gv

Sarasota
Ocean View
This Gulf View unit is warm and cozy with it's nice neutral and brown decor. This unit has tile thro...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Water's Edge 209 North

Holmes Beach
Enjoy the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month...

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Condo 2 / 2 / 6

Online Booking

$240 - $430
Per Night

$1680 - $3010
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...

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Home 3 / 2 / 6

Online Booking

$300 - $600
Per Night

$2100 - $4200
Per Week

 
 

Sandy Pointe Unit 202

Holmes Beach
Beach Access
The peaceful and airy feeling “Sandy Point 202” is a condo style Holmes Beach vacation home located ...

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Condo 2 / 2 / 6

Online Booking

$165 - $245
Per Night

$1155 - $1715
Per Week

 
 

River Pointe 01

Bradenton
Lake View
River Pointe is a boating community along the Manatee River with nearby River Isles Golf Course.Grea...

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Home 4 / 2 / 8

Online Booking

$170 - $245
Per Night

$1190 - $1715
Per Week

 
 

House Of The Sun #203Gs

Sarasota
Virtual Tour This "NEWLY RENOVATED" Gulf Side unit has new tile in the common areas and b...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

SeaBreeze Sands

Holmes Beach
Sea Breeze Sands is a fabulous three story vacation home sitting right across from the Gulf of Mexic...

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Home 3 / 3.5 / 6

Online Booking

$300 - $600
Per Night

$2100 - $4200
Per Week

 
 

Grant's View

Anna Maria
Grant's View is a private bay front home is located on the Tampa Bay where you will enjoy the amazin...

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Cottage 2 / 2 / 6

Online Booking

$205 - $450
Per Night

$1435 - $3150
Per Week

 
 

Quiet Hideaway

Holmes Beach
Welcome to Hideaway a new and beautifully done duplex! 1050 square feet under A/C Great looking vac...

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Home 2 / 2 / 6

Online Booking

$200 - $375
Per Night

$1400 - $2625
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...

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Home 3 / 2 / 6

Online Booking

$335 - $500
Per Night

$2345 - $3500
Per Week

 
 

The Anna Maria Island Beach Paradise 6

Holmes Beach
Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you ar...

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Condo 2 / 2 / 6

Online Booking

$225 - $420
Per Night

$1575 - $2940
Per Week

 
 

House Of The Sun #309Gv

Sarasota
Ocean View
You will feel right at home in this cozy Gulf View unit. It has new leather furniture and a 42” LCD...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Beach View 5

Holmes Beach
Beach View is one of the favorite spots for visitors wanting to experience what local island life is...

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Condo 2 / 2 / 6

Online Booking

$180 - $305
Per Night

$1295 - $2135
Per Week

 
           
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