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 #316Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #210Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
La Casa LaMar
3 bedroom Holmes Beach Condo Vacation Rental Condo
3 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

House Of The Sun #316Gf

Sarasota
Ocean Front
This Gulf Front unit has tile throughout the common areas, and carpet in the bedrooms. Both bathroom...

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Condo 2 / 2 / 4

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
 

House Of The Sun #210Gv

Sarasota
Ocean View
Contemporary and stylish Unit 210 provides the utmost in an island retreat. Relax and enjoy fabulous...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #406Gs

Sarasota
Virtual Tour Newly renovated throughout this 4th Floor Gulf Side unit boasts beautiful designer til...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
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 #504Gs

Sarasota
This Gulf Side unit has been recently renovated with tile throughout the common areas and contempora...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

 
 

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 #205Gs

Sarasota
This Gulf Side unit has teal-blue carpet in the living room and bedrooms and tile in the foyer and h...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Almost Heaven

Holmes Beach
3 Bedroom, 2 Bath (sleeps 6) - "Almost Heaven" - 205 72nd Street, Holmes Beach Welcome to Almost He...

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Home 3 / 2 / 6

Online Booking

$230 - $385
Per Night

$1610 - $2695
Per Week

 
 

Bay Oaks B-52, 2 Bedrooms, Updated Condo, Sleeps 6

Siesta Key
Beach Access
Featured on HGTV's Beachfront Bargain Hunt TV show! With views over a sunny, peek a boo view of the ...

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Condo 2 / 2.5 / 6

Online Booking

$121 - $416
Per Night

$564 - $672
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

 
 

Midnight Pass Condo #411GV

Sarasota
This Gulf View unit has tile throughout all common areas and blue carpet in the bedrooms. The color ...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
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

 
 

The Anna Maria Island Beach Palms 7A

Bradenton Beach
The Anna Maria Island Beach Palms 7A is located with-in walking distance of Anna Maria Island's best...

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Condo 2 / 2 / 6

Online Booking

$220 - $420
Per Night

$1540 - $2940
Per Week

 
 

Inlet 21, 2 Bedrooms, Lagoon and Gulf Views, Pool, Wifi, ...

Sarasota
Are you ready for a great escape? If so, Inlet 21 is the perfect spot for you. This unit has beautif...

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Condo 2 / 2 / 6

Online Booking

$100 - $241
Per Night

$700 - $1686
Per Week

 
 

Midnight Pass Condo #509GV

Sarasota
This newly renovated Gulf View unit has new stainless steel appliances in the kitchen with granite c...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

Midnight Pass Condo #312GV

Sarasota
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

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

Midnight Pass Condo #207GS

Sarasota
This Gulf Side unit has a lot of pizazz!! The unit has brand new tile in the kitchen and living area...

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Condo 2 / 2 / 4

Online Booking

$215 - $310
Per Night

$1505 - $2170
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

 
 

Shoreline Terrace

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

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Cottage 4 / 2.5 / 8

Online Booking

$320 - $850
Per Night

$2240 - $5950
Per Week

 
 

Misty Beach

Holmes Beach
Island life is simpler and slower than life anywhere else in the world. It's just hard to get too wo...

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Home 2 / 2 / 6

Online Booking

$180 - $360
Per Night

$1260 - $2520
Per Week

 
 

Almost Gulf Front

Holmes Beach
A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates u...

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Home 6 / 4.5 / 12

Online Booking

$410 - $1185
Per Night

$2870 - $8295
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. ...

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Home 3 / 2.5 / 8

Online Booking

$240 - $425
Per Night

$1680 - $2975
Per Week

 
 

Down by the Sea

Anna Maria
Down by the Sea is a lovely ground level vacation rental home in a quiet Anna Maria City neighborhoo...

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Home 3 / 2 / 6

Online Booking

$205 - $340
Per Night

$1435 - $2380
Per Week

 
 

My Sisters Beach House

Anna Maria
This is simply the most luxurious 5-bedroom canal-front home available on the island. When you arriv...

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Home 5 / 3.5 / 12

Online Booking

$530 - $1230
Per Night

$3710 - $8610
Per Week

 
           
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