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

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Featured Listings
 
House Of The Sun #511Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 2
More Info
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 #414Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

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

 
 

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

 
 

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 #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

 
 

New + modern Villa with gorgeous pool area near Gulf beaches

Venice
Golf nearby, Ocean nearby
!!! PLEASE CHECK AVAILABILITY BEFORE SENDING AN INQUIRY! THANK YOU !!! We would like to invite you ...

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Villa 3 / 2 / 6

$115 - $165
Per Night

$800 - $1350
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 - $179
Per Night

$500 - $1250
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

 
 

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 #311Gv

Sarasota
Ocean View
This Gulf View unit is warm and cozy with it's nice neutral and brown decor. This unit has tile thro...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Venice Harbor 606, 2 Bedrooms, Pet Friendly, Wifi, Sleeps 4

Venice
Ocean View
On a sunny island with a nearby beach, you’ll sleep comfortably in the heart of Venice Island, FL. J...

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Home 2 / 1.5 / 4

Online Booking

$85 - $259
Per Night

$595 - $1684
Per Week

 
 

Venice Avalon Home, 3 Bedrooms, Pet Friendly, Wifi, Sleeps 8

Venice
A lovely and spacious house for ten, this Avalon Venice home boasts all manner of new additions and ...

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Home 3 / 2 / 8

Online Booking

$71 - $179
Per Night

$500 - $1250
Per Week

 
 

House Of The Sun #203Gs

Sarasota
Virtual Tour This "NEWLY RENOVATED" Gulf Side unit has new tile in the common areas and b...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Bayshore Home, 4 Bedrooms, Private Heated Pool, Hdtv, Wif...

Venice
Walk to downtown Venice in less than five minutes - it’s only two blocks away. For any other require...

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Home 4 / 2 / 12

Online Booking

$121 - $399
Per Night

$850 - $2594
Per Week

 
 

Nantucket Home, 2 Bedrooms, Private Pool, Fenced Yard, Sl...

Venice
Step into the good life, in this Nantucket home in Venice, FL. A great choice if you’re looking for ...

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Home 2 / 2 / 6

Online Booking

$48 - $179
Per Night

$338 - $1250
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

 
 

Sunset Royale 200, 2 Bedrooms, Gulf View, 2nd Floor, Slee...

Siesta Key
Beach Access, Ocean View
Sunset Royale 200 is literally across the street from Siesta Beach and the Gulf of Mexico. The only ...

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Condo 2 / 2 / 4

Online Booking

$114 - $376
Per Night

$795 - $2634
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 #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

 
 

House Of The Sun #308Gv

Sarasota
Ocean View
Virtual Tour You'll know you're on vacation but with all of the comforts of home! Enjoy this beauti...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Gulf Holidays 15, 1 Bedroom, 2nd Floor, Heated Pool, Slee...

Siesta Key
Beach Access
Siesta Key is one of the premier beach vacation destinations in America. When you stay at Gulf Holid...

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Condo 1 / 1 / 4

Online Booking

$71 - $242
Per Night

$495 - $1695
Per Week

 
 

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

Siesta Key
Beach Access
Sun seekers Delight! Enjoy your morning coffee looking at the palms and oaks lining the boat basin f...

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Condo 2 / 1.5 / 4

Online Booking

$71 - $242
Per Night

$495 - $1695
Per Week

 
 

House Of The Sun #409Gv

Sarasota
Ocean View
This Gulf View unit was recently renovated and has recently added a new sofa and chair. There is ti...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Casa de Mariposa 5542, 3 Bedroom, Gulfview, Elevator, Hea...

Siesta Key
Beach Access, Ocean View
Casa de Mariposa 5542 is a beautifully designed 3 bedroom, 3 bathroom home with a gulf view, shared ...

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Home 3 / 3 / 8

Online Booking

$318 - $888
Per Night

$2225 - $4550
Per Week

 
 

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

Nokomis
If you’re looking for a longer-term rental, you want the house to be a true home away from home. Bui...

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Home 3 / 2 / 6

Online Booking

$152 - $321
Per Night

$1063 - $2250
Per Week

 
 

Lakeside House, 4 Bedrooms, Private Heated Pool, Hdtv, Wi...

Venice
The boundaries between indoor and outdoor are delightfully blurred in our spacious Venice Lakeside H...

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Home 4 / 2 / 8

Online Booking

$71 - $214
Per Night

$500 - $1500
Per Week

 
           
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