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 #501Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #405Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Bay Oaks B-52, 2 Bedrooms, ...
2 bedroom Siesta Key Condo Vacation Rental Condo
2 BR/ 2.50 BA Sleeps 6
More Info
 
 
 
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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 #405Gs

Sarasota
Virtual Tour This Gulf Side unit will make you feel right at home at the beach with it's sand &...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #301Gs

Sarasota
Enter your own tropical paradise when entering this Gulf Side unit! The beautiful hand painted mura...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

 
 

Modern Villa - Pool, Hot Tub, Water View + Golf

Sarasota
Golf on site, Lake Front, Lake View, Ocean nearby
Sarasota Private 2-Bedroom, 2-Bathrooom Contemporary Villa at Heritage Oaks Golf & Country Club • P...

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Villa 2 / 2 / 4

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House Of The Sun #215Gf

Sarasota
Ocean Front
Relax in your own beachfront paradise condo. Enjoy a special treat, watching dolphins, or sun bathin...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
 

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 #302Gs

Sarasota
Virtual Tour The gulf side unit has recently been updated with new kitchen appliances, soft close c...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Casa Del Sol C

Bradenton Beach
Includes swimming pool and partial views of the gulf, and only 1/2 block from the incredible beaches...

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Cottage 2 / 1 / 4

Online Booking

$130 - $210
Per Night

$910 - $1470
Per Week

 
 

Rosedale 01

Bradenton
This stunning 3 bedroom pool and spa home will make you feel like you are staying in an art gallery,...

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Home 3 / 3.5 / 6

Online Booking

$235 - $285
Per Night

$1645 - $1995
Per Week

 
 

Crescent Street 1138 A, 2 bedrooms, pool, walk to the beach

Siesta Key
When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes ...

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Condo 2 / 1 / 6

Online Booking

$99 - $366
Per Night

$695 - $2561
Per Week

 
 

The Anna Maria Island Beach Paradise 5

Holmes Beach
The Anna Maria Island Beach Paradise 5 condo is located directly in the middle of beautiful Anna Mar...

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Condo 2 / 2 / 6

Online Booking

$225 - $420
Per Night

$1575 - $2940
Per Week

 
 

Beach View 207

Bradenton Beach
Beach Access
The Anna Maria Island Beach View 207 is a beautiful recently remodeled two bedroom, two bathroom con...

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Condo 2 / 2 / 5

Online Booking

$180 - $420
Per Night

$1260 - $2940
Per Week

 
 

River Strand 06

Bradenton
Enjoy your Bradenton vacation rental and plenty of golf within 20 minutes of Florida`s Gulf Coast be...

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Home 3 / 2 / 6

Online Booking

$185 - $255
Per Night

$1295 - $1785
Per Week

 
 

The Anna Maria Island Beach Paradise 10

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 0 / 1.5 / 3

Online Booking

$150 - $180
Per Night

$1050 - $1260
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

 
 

House Of The Sun #315Gf

Sarasota
Ocean Front
This newly rennovated Gulf Front unit will make you feel right at home with it's warm and cozy decor...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
 

House Of The Sun #212Gv

Sarasota
Ocean View
Virtual Tour This freshly painted Gulf View unit has carpet in the living room and both bedrooms. N...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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

 
 

The Anna Maria Island Beach Castaway 2

Holmes Beach
The Anna Maria Island Beach Castaway 1 is locateddirectly in the middle of Anna Maria Island and is ...

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Condo 2 / 1 / 6

Online Booking

$165 - $420
Per Night

$1155 - $2940
Per Week

 
 

Siesta Dunes Beach 201, 2 Bedrooms, Large Heated Pool, Sp...

Siesta Key
Beach Access
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for ...

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Condo 2 / 2 / 6

Online Booking

$114 - $356
Per Night

$795 - $2495
Per Week

 
 

Sabal Harbour 02

Bradenton
Modern and comfortable furnishings with a very large open floor plan makes this vacation home ideal ...

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Home 4 / 2 / 8

Online Booking

$185 - $255
Per Night

$1295 - $1785
Per Week

 
 

The Anna Maria Island Beach View 209

Bradenton Beach
Beach Access
The Anna Maria Island Beach View #209 is located with-in walking distance of Anna Maria Island's bes...

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Condo 2 / 2 / 6

Online Booking

$180 - $420
Per Night

$1260 - $2940
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

 
 

Gulf Sands Condo Beach Front

Holmes Beach
Beach Front, Ocean View
700 ft. of pristine beach frontage, only 16 Units! This beachfront condo is located right on Holmes ...

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Condo 2 / 2 / 4

Online Booking

$205 - $275
Per Night

$1435 - $1925
Per Week

 
           
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