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 #316Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 4
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 #510Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

House Of The Sun #306Gs

Sarasota
This Gulf Side unit is a beach paradise! This unit has new tile throughout the common areas, beige ...

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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 #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

 
 

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

 
 

Poco Place, 2 Bedrooms, Wifi, 2 Blocks to Beach, Sleeps 6

Nokomis
You’ll be just two blocks from the Gulf when you vacation at Poco Place, a small home tucked away on...

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Home 2 / 1 / 6

Online Booking

$84 - $213
Per Night

$586 - $1490
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

 
 

Flamingo Home, 3 Bedrooms, Private Heated Pool, Pet Frien...

Venice
As you might expect, the private backyard at Flamingo House brims with color and life. Palms and tro...

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Home 3 / 2 / 8

Online Booking

$102 - $261
Per Night

$712 - $1829
Per Week

 
 

Palm Bay Club G46, 1 Bedroom, 40" Hdtv, Heated Pool, Wifi...

Siesta Key
Beach Access
With the top-rated beach in the country in your backyard, Palm Bay Club G46 delivers the perfect Gul...

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Condo 1 / 1 / 4

Online Booking

$107 - $246
Per Night

$750 - $1725
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

$147 - $418
Per Night

$1028 - $2928
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

 
 

Rialto Mansion, 6 Bedrooms, Private Heated Pool, Pet Frie...

Venice
Need a vacation home that’s within walking distance of the beach, shops, and restaurants, and large ...

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Home 6 / 3.5 / 14

Online Booking

$215 - $533
Per Night

$1504 - $3729
Per Week

 
 

White Sands Village 205, 2 Bedrooms, Heated Pool, Wifi, S...

Siesta Key
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor con...

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Condo 2 / 2 / 6

Online Booking

$102 - $219
Per Night

$712 - $1532
Per Week

 
 

Anchorage 904, 2 Bedrooms, Gorgeous Views, Wifi, Pool, Sa...

Sarasota
Beach Access, Ocean View
You’ll be living the high life at Anchorage 904—literally and figuratively. Located on the 9th floor...

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Condo 2 / 2 / 6

Online Booking

$128 - $330
Per Night

$895 - $2312
Per Week

 
 

Gulf and Bay Club: Bayside 1226, 2 Bedrooms, Sleeps 6, 2 ...

Siesta Key
Beach Access, Ocean View
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfec...

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Condo 2 / 2 / 6

Online Booking

$107 - $300
Per Night

$750 - $2100
Per Week

 
 

Siesta Dunes Beach 38A, 2 Bedrooms, Ground Floor, Heated ...

Siesta Key
Live the tropical life in this incredible modern condo! From the large wooden deck to the heated poo...

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Condo 2 / 2 / 6

Online Booking

$124 - $330
Per Night

$868 - $2312
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

 
 

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 - $274
Per Night

$795 - $1917
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

 
 

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 - $161
Per Night

$500 - $1125
Per Week

 
 

Gulf and Bay Club 108D, 2 Bedroom, Beach Front, Ground Fl...

Siesta Key
Beach Access, Beach Front, Ocean View
Want to get away from everyday life and enjoy a month alongside the #1 beach in the USA? Gulf and Ba...

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Condo 2 / 2 / 4

Online Booking

$118 - $289
Per Night

$827 - $2025
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 - $266
Per Night

$595 - $1861
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 #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

 
 

Crescent Street 1138 A, 2 bedrooms, pool, walk to the beach

Siesta Key
When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes ...

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Condo 2 / 1 / 6

Online Booking

$114 - $274
Per Night

$795 - $1917
Per Week

 
 

Crescent Street Manor, 3 Bedrooms, Walk to Beach, Private...

Siesta Key
When you stay at Crescent Street Manor, you can walk to the east side of Siesta Key in just minutes ...

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Condo 3 / 2 / 10

Online Booking

$199 - $659
Per Night

$1395 - $4615
Per Week

 
           
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