Osprey
 
 
 
 
 
 
Browse the listings near Osprey or filter by a nearby city from the list below.

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Featured Listings
 
Poco Place, 2 Bedrooms, Wi ...
2 bedroom Nokomis Home Vacation Rental Home
2 BR/ 1.00 BA Sleeps 6
More Info
House Of The Sun #507Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
More Info
House Of The Sun #211Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
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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 #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 #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 #507Gv

Sarasota
Ocean View
This newly renovated Gulf View unit newly installed stainless steel appliances in the kitchen with g...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

3Br/2Ba private home walking distance to beach & restaurants

Nokomis
Beach Access
This hidden jewel is just a short walk to Nokomis public beach, Casey Key, public boat ramp, inter-c...

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Home 3 / 2 / 6

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House Of The Sun #211Gs

Sarasota
Welcoming neutral tones lend comfort and warmth to this Gulf Side unit boasting much-requested tile ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Poco Place, 2 Bedrooms, Wifi, 2 Blocks to Beach, Sleeps 8

Nokomis
Get up in the morning and throw on your swimsuit, some shorts, and flip-flops - it’s just 2 blocks t...

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Home 2 / 1 / 6

Online Booking

$71 - $169
Per Night

$500 - $1181
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

 
 

Albee Sunset Cottage, 2 Bedrooms, Pet Friendly, Wifi, Sle...

Nokomis
Just one and a half blocks to gorgeous Nokomis Beach, this beach house for eight truly delivers the ...

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Home 2 / 1 / 8

Online Booking

$71 - $169
Per Night

$500 - $1181
Per Week

 
 

Harbor Paradise Home, 4 Bedrooms, Private Heated Pool, Hd...

Venice
A big house for a big group, this gorgeous Venice island paradise beach retreat is an ideal base for...

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Home 4 / 3 / 12

Online Booking

$171 - $418
Per Night

$1195 - $2928
Per Week

 
 

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 #510Gv

Sarasota
Ocean View
Virtual Tour This newly renovated Gulf View unit has tile throughout the common areas and carpet in...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Baycrest Home, 3 Bedrooms, Private Heated Pool, Wifi, Sle...

Venice
Ideal for a large family gathering or reunion, this charming beach house for ten can be easily rente...

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Home 3 / 2 / 10

Online Booking

$142 - $361
Per Night

$995 - $2528
Per Week

 
 

House Of The Sun #312Gv

Sarasota
Ocean View
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

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, Wifi, Sle...

Siesta Key
Enjoy an amazing location and luxurious accommodations! With indoor and outdoor seating, 3 heated po...

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Condo 2 / 2 / 6

Online Booking

$114 - $306
Per Night

$795 - $2142
Per Week

 
 

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

Sarasota
Ocean View
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

$127 - $203
Per Night

$889 - $1418
Per Week

 
 

Gulf and Bay Club 102B, Beach Front, 2 Bedrooms, Ground F...

Siesta Key
Beach Access, Beach Front, Ocean View
Ready to spend 28 days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This gro...

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Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2126
Per Week

 
 

Gulf and Bay Club 409B, 2 Bedrooms, Beach Front, Heated P...

Siesta Key
Beach Access, Ocean View
Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf a...

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Condo 2 / 2 / 4

Online Booking

$161 - $321
Per Night

$1125 - $2244
Per Week

 
 

Twin Palms 5, 1 Bedroom, Ground Floor, Heated Pool, Wifi,...

Siesta Key
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA when you stay at Twin...

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Condo 1 / 1 / 4

Online Booking

$107 - $275
Per Night

$750 - $1926
Per Week

 
 

Parkdale Home, 4 bedrooms, Private Heated Pool, Hdtv, Wifi

Venice
Beach or pool? Pool or beach? You’ll never have to choose at Parkdale Venice House. This gorgeous 4-...

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Home 4 / 3 / 12

Online Booking

$150 - $380
Per Night

$1050 - $2661
Per Week

 
 

Golden Sunrise House, 3 bedrooms, Private Heated Pool, Sm...

Nokomis
If you have dreamed of vacationing on the water, Golden Sunrise is the house for you! Located lakesi...

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Home 3 / 2 / 6

Online Booking

$78 - $194
Per Night

$549 - $1358
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

 
 

Siesta Key Excelsior 306, 3 Bedrooms, Pools, Tennis, Slee...

Siesta Key
Beach Access
With spectacular views of the beautiful trees, pond, pool and peek a boo view of the Intracoastal, y...

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Condo 3 / 2 / 6

Online Booking

$129 - $369
Per Night

$900 - $2583
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 #216Gf

Sarasota
Ocean Front
This newly renovated Gulf Front unit offers pristine views of the beautiful turquoise waters and whi...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
           
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