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 #509Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #309Gv
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 #202Gs

Sarasota
This Gulf Side unit is bright and airy accented with blues and browns with tile throughout. There ar...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

 
 

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

 
 

House Of The Sun #205Gs

Sarasota
This Gulf Side unit has teal-blue carpet in the living room and bedrooms and tile in the foyer and h...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Modern Villa - Pool, Hot Tub, Water View + Golf

Sarasota
Golf on site, Lake Front, Lake View, Ocean nearby
Sarasota Private 2-Bedroom, 2-Bathrooom Contemporary Villa at Heritage Oaks Golf & Country Club • P...

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Villa 2 / 2 / 4

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Owner
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For Rates

 
 

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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Owner
Directly
For Rates

 
 

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 #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

 
 

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 - $161
Per Night

$500 - $1125
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

$126 - $399
Per Night

$882 - $2793
Per Week

 
 

Midnight Pass Condo #313GV

Sarasota
Feel right at home in this Gulf view second from the front unit, just steps away from the pool, tenn...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

Midnight Pass Condo #208GS

Sarasota
All new ! Totally renovated from ceiling to tile floor and everything in between! Sunny yellow fresh...

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Condo 2 / 2 / 4

Online Booking

$215 - $310
Per Night

$1505 - $2170
Per Week

 
 

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

Siesta Key
Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do...

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Condo 2 / 2 / 6

Online Booking

$104 - $416
Per Night

$729 - $2911
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

 
 

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

$167 - $479
Per Night

$1172 - $3353
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

$95 - $383
Per Night

$668 - $2680
Per Week

 
 

Midnight Pass Condo #302GS

Sarasota
The gulf side unit has recently been updated with new kitchen appliances, soft close cabinet doors, ...

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Condo 2 / 2 / 4

Online Booking

$215 - $310
Per Night

$1505 - $2170
Per Week

 
 

Polynesian Gardens Villa P6, 2 Bedrooms, Heated Pool, Car...

Siesta Key
Looking for a home away from home as you embark upon your upcoming vacation, Polynesian Gardens Vill...

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Condo 2 / 2 / 4

Online Booking

$102 - $400
Per Night

$714 - $2800
Per Week

 
 

Siesta Dunes 8-205, 2nd Floor, Spa, Beach, Large Heated Pool

Siesta Key
Beach Access, Ocean View
Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice fo...

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Condo 2 / 2 / 4

Online Booking

$185 - $551
Per Night

$1095 - $1350
Per Week

 
 

Midnight Pass Condo #216GF

Sarasota
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

$300 - $425
Per Night

$2100 - $2975
Per Week

 
 

Aurora Seabreeze, 3 Bedroom, Fenced Yard, Heated Pool, Wi...

Venice
Ideal for families gathering from across the country and for vacations with many generations, Aurora...

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Home 3 / 2 / 10

Online Booking

$119 - $384
Per Night

$836 - $2689
Per Week

 
 

Midnight Pass Condo #215GF

Sarasota
Relax in your own beachfront paradise condo. Enjoy a special treat, watching dolphins, or sun bathin...

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Condo 2 / 2 / 6

Online Booking

$300 - $425
Per Night

$2100 - $2975
Per Week

 
 

Midnight Pass Condo #209GS

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

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Condo 2 / 2 / 4

Online Booking

$215 - $310
Per Night

$1505 - $2170
Per Week

 
 

House Of The Sun #303Gs

Sarasota
Virtual Tour This Gulf Side unit has beige carpet throughout and is decorated with light shades of ...

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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
Hop into the Rialto Mansion, a 6-bedroom beauty on gorgeous Venice Island. Just a few blocks walk to...

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Home 6 / 3.5 / 14

Online Booking

$215 - $567
Per Night

$1508 - $3972
Per Week

 
           
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