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 #305Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
House Of The Sun #207Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Fountain Head 2
2 bedroom Holmes Beach Home Vacation Rental Home
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

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 #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

$247 - $247
Per Night

$1196 - $1732
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 #304Gs

Sarasota
Virtual Tour Freshly Painted and Ready for Relaxation!!! This Gulf Side unit is very soothing with ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #209Gs

Sarasota
This Gulf Side unit has a neutral color scheme of browns and tans in the living room, while the bed...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #208Gs

Sarasota
Virtual Tour All NEW! Totally renovated from ceiling to tile floor and everything in between! Sunny...

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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

 
 

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

 
 

Sunset Villa 3

Bradenton Beach
Sunset Villa awaits the vacationer in you. Located in this well-kept condo complex directly across f...

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Condo 2 / 1.5 / 4

Online Booking

$170 - $290
Per Night

$1190 - $2030
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

$335 - $580
Per Night

$2345 - $4060
Per Week

 
 

Casa Playa East

Bradenton Beach
Beach Access
This rental home on Anna Maria Island sleeps up to 10 and comes fully equipped. This Bradenton Beac...

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Home 4 / 3.5 / 11

Online Booking

$275 - $670
Per Night

$1925 - $4690
Per Week

 
 

LaMadeira Unit A

Holmes Beach
(3) Bedroom, (3) Bath (Sleeps 6) – “LaMedeira”- 305 64th St unit A in Holmes Beach. “LaMedeira” is ...

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Home 3 / 3 / 6

Online Booking

$265 - $535
Per Night

$1855 - $3745
Per Week

 
 

Lushly Landscaped Three Bedroom Pool Duplex

Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time s...

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Home 3 / 2.5 / 6

Online Booking

$210 - $355
Per Night

$1505 - $2485
Per Week

 
 

Runaway Bay

Bradenton Beach
You’ll find the perfect Anna Maria Island couples getaway at Runaway Bay 256! This stylish and comfo...

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Condo 1 / 1 / 2

Online Booking

$115 - $180
Per Night

$805 - $1260
Per Week

 
 

Casa Sierra

Holmes Beach
Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful A...

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Home 2 / 2 / 6

Online Booking

$170 - $290
Per Night

$1190 - $2030
Per Week

 
 

Water's Edge 205 South

Holmes Beach
Direct gulf front one bedroom and one and a half bath condo in desirable Water's Edge complex which ...

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Condo 1 / 1.5 / 4

Online Booking

$160 - $265
Per Night

$1120 - $1855
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 2 / 1.5 / 6

Online Booking

$150 - $180
Per Night

$1050 - $1260
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

 
 

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

 
 

Blue Manatee Retreat

Holmes Beach
Updated Holmes Beach Island home just steps to the Gulf of Mexico beaches. Enjoy this vacation renta...

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Home 3 / 3 / 6

Online Booking

$245 - $440
Per Night

$1715 - $3080
Per Week

 
 

Gulf Place

Holmes Beach
Beach Front
3 Bedroom, 2 Bath (Sleeps 6) – “Gulf Place” – 6700 Gulf Drive Unit 14 in Holmes Beach. Offering eve...

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Condo 3 / 2 / 6

Online Booking

$240 - $440
Per Night

$1680 - $3080
Per Week

 
 

River Strand 24

Bradenton
Fully equipped, includes small private pool, and be sure to enjoy downtown Bradenton and the Boardwa...

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Home 3 / 2 / 6

Online Booking

$185 - $255
Per Night

$1295 - $1785
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

 
 

North Beach Village Unit 72

Holmes Beach
 3 Bedroom, 2.5 Bath (Sleeps 6) - “North Beach Village” 6250 Holmes Boulevard unit 72 in Holmes Beac...

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Home 3 / 2.5 / 6

Online Booking

$170 - $290
Per Night

$1190 - $2030
Per Week

 
 

Palm Isle 3204

Holmes Beach
perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bed...

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Cottage 2 / 1 / 6

Online Booking

$150 - $255
Per Night

$1050 - $1785
Per Week

 
           
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