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 #503Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #208Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Anna Cabana Bungalow #3
1 bedroom Holmes Beach Home Vacation Rental Home
1 BR/ 1.00 BA Sleeps 2
More Info
 
 
 
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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

 
 

House Of The Sun #411Gv

Sarasota
Ocean View
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

$289 - $289
Per Night

$1380 - $2021
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

 
 

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

 
 

House Of The Sun #503Gs

Sarasota
Virtual Tour This Gulf side unit has beautiful tile throughout the common area and bathrooms. Off w...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

 
 

House Of The Sun #401Gs

Sarasota
This freshly painted Gulf Side unit has new berber carpet throughout the common areas and bedrooms, ...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Midnight Cove II 432, 2 Bedrooms, Large Heated Pool, Spa,...

Siesta Key
Beach Access
From the spacious balcony of this 3rd-floor condo, you can enjoy sun or shade, watch exotic birds vi...

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Condo 2 / 1.5 / 4

Online Booking

$114 - $274
Per Night

$795 - $1917
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

$170 - $384
Per Night

$753 - $896
Per Week

 
 

Bayview Condo G

Bradenton Beach
Bayview Condo G is a beautiful two bedroom two bath condo located at 108 9th Street South in Bradent...

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Condo 2 / 2 / 6

Online Booking

$190 - $440
Per Night

$1330 - $3080
Per Week

 
 

Four Beach Lovers 2

Holmes Beach
Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, thi...

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Home 1 / 1 / 4

Online Booking

$180 - $330
Per Night

$1260 - $2310
Per Week

 
 

Good Times Both Units

Bradenton Beach
The Good Times A and B, located at 303 Highland Avenue in Bradenton Beach is a quiet, duplex with fo...

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Home 4 / 4 / 8

Online Booking

$265 - $490
Per Night

$1855 - $3430
Per Week

 
 

Bay Oaks D-42, 2 Bedrooms, Siesta Key Florida, Updated Condo

Siesta Key
With 2 bedrooms and 2.5 bathrooms, Bay Oaks D-42 can accommodate a family of 5 or 2 couples with equ...

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Condo 2 / 2.5 / 5

Online Booking

$99 - $219
Per Night

$695 - $1532
Per Week

 
 

Anna Cabana Resort

Holmes Beach
The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all locat...

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Home 5 / 5 / 16

Online Booking

$490 - $925
Per Night

$3430 - $6475
Per Week

 
 

Ss Salamander North

Holmes Beach
Welcome to the SS Salamander, North unit at 121 50th Street in Holmes Beach. This recently updated t...

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Home 2 / 1.5 / 6

Online Booking

$175 - $295
Per Night

$1225 - $2065
Per Week

 
 

Sandy Pointe 210

Holmes Beach
Sandy Pointe Condo #210, at 3607 East Bay Drive is a cheerful, two bedroom and two bath condo in a s...

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Condo 2 / 2 / 6

Online Booking

$105 - $215
Per Night

$735 - $1505
Per Week

 
 

Jamaica Royale 91, 2 Bedrooms, 3 Heated Pools, Wifi, Slee...

Siesta Key
In this handy ground-floor condo, you're just a short walk away from gorgeous Crescent Beach, the je...

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Condo 2 / 2 / 6

Online Booking

$114 - $274
Per Night

$795 - $1917
Per Week

 
 

Beach Sands 201

Bradenton Beach
Beach Access
The Anna Maria Island Beach Sands #201 is located with-in walking distance of Anna Maria Island's be...

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Condo 2 / 2 / 6

Online Booking

$175 - $400
Per Night

$1225 - $2800
Per Week

 
 

Seagrass Flats 3

Bradenton Beach
Seagrass Flats Condo #3 is a upper level, pool side unit located at 101 25th Street North in Bradent...

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Condo 2 / 2 / 6

Online Booking

$140 - $230
Per Night

$980 - $1540
Per Week

 
 

Alamanda Villas 6

Holmes Beach
Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featurin...

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Condo 1 / 1 / 4

Online Booking

$170 - $315
Per Night

$1190 - $2205
Per Week

 
 

Tiki

Holmes Beach
The Tiki, located at 3214 Gulf Drive in Holmes Beach is a spectacular three bedroom, two bath home d...

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Home 3 / 2 / 8

Online Booking

$325 - $630
Per Night

$2275 - $4410
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

 
 

Blue Dolphin Inn - Heron Up

Anna Maria
Beach Access
The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Mari...

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Home 2 / 2 / 6

Online Booking

$155 - $305
Per Night

$1085 - $2135
Per Week

 
 

Runaway Bay 207

Bradenton Beach
Beach Access
Runaway Bay condominium #207, located at 1801 Gulf Drive in northern Bradenton Beach, is a comfortab...

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Condo 2 / 2 / 6

Online Booking

$130 - $250
Per Night

$910 - $1750
Per Week

 
 

The Anna Maria Island Beach Sands 203

Bradenton Beach
Beach Access
FAMILY/CHILD FRIEDLY CONDOMINIUM. Surrounded by water with the Gulf of Mexico to the west, the Intr...

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Condo 2 / 2 / 4

Online Booking

$175 - $400
Per Night

$1225 - $2800
Per Week

 
           
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