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

Refine Your Search:
Destination
Check-In Check-Out
Amenities
Enter Keywords:
 
 
 
 
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 #304Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
House Of The Sun #506Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

House Of The Sun #506Gs

Sarasota
Virtual Tour A 2 bedroom 2 bath accommodation on the 5th floor, (accessible via two outside elevato...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #304Gs

Sarasota
Virtual Tour Freshly Painted and Ready for Relaxation!!! This Gulf Side unit is very soothing with ...

View Details and Book Online    Send Inquiry
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
You’ll be just two blocks from the Gulf when you vacation at Poco Place, a small home tucked away on...

View Details and Book Online    Send Inquiry
Home 2 / 1 / 6

Online Booking

$103 - $213
Per Night

$723 - $1490
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$343 - $343
Per Night

$1693 - $2400
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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 ...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Beachaven 52, 1 bedroom, Ground Floor, Pool, Sleeps 4

Siesta Key
Ocean View
Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery ...

View Details and Book Online    Send Inquiry
Condo 1 / 2 / 4

Online Booking

$113 - $203
Per Night

$793 - $1418
Per Week

 
 

House Of The Sun #412Gv

Sarasota
Ocean View
This Gulf View unit is nice and cozy with it's warm decor. This unit has tile throughout the kitche...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Harbor Duplex, 3 Bedrooms, Walk to Beach, Wifi, Sleeps 10

Venice
You’ve found it – the perfect site for your two-family getaway in Venice, Florida. Harbor Duplex is ...

View Details and Book Online    Send Inquiry
Home 3 / 2.5 / 8

Online Booking

$157 - $359
Per Night

$1100 - $2515
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$114 - $274
Per Night

$795 - $1917
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...

View Details and Book Online    Send Inquiry
Condo 1 / 1 / 4

Online Booking

$107 - $246
Per Night

$750 - $1725
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$107 - $219
Per Night

$750 - $1532
Per Week

 
 

Harbor Towers Yacht & Racquet 324, 1 Bedroom, Heated Pool...

Siesta Key
Beach Access
Discover the power that a change of scenery can have: steal away to this charming pied-a-terre just ...

View Details and Book Online    Send Inquiry
Condo 1 / 1 / 4

Online Booking

$107 - $219
Per Night

$750 - $1532
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 ...

View Details and Book Online    Send Inquiry
Condo 3 / 2 / 10

Online Booking

$199 - $659
Per Night

$1395 - $4615
Per Week

 
 

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

Siesta Key
Welcome to your home in paradise! This standalone 2-bedroom villa offers privacy and relaxation for ...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$100 - $191
Per Night

$700 - $1339
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...

View Details and Book Online    Send Inquiry
Condo 2 / 1.5 / 4

Online Booking

$114 - $274
Per Night

$795 - $1917
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
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...

View Details and Book Online    Send Inquiry
Condo 1 / 1 / 4

Online Booking

$107 - $246
Per Night

$750 - $1725
Per Week

 
 

Euclid Home, 3 Bedrooms, Private Heated Pool, Wifi, Sleeps 8

Venice
Located in a laid-back residential area, pet-friendly Euclid Home is ideal for a family vacation—not...

View Details and Book Online    Send Inquiry
Home 3 / 2 / 8

Online Booking

$120 - $248
Per Night

$843 - $1738
Per Week

 
 

House Of The Sun #314Gv

Sarasota
Ocean View
This Gulf View unit has tile throughout common areas, 2 full size sofas and a leather recliner. The ...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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...

View Details and Book Online    Send Inquiry
Home 4 / 2 / 8

Online Booking

$93 - $236
Per Night

$650 - $1654
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-...

View Details and Book Online    Send Inquiry
Home 4 / 3 / 12

Online Booking

$150 - $380
Per Night

$1050 - $2661
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2126
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...

View Details and Book Online    Send Inquiry
Home 2 / 1.5 / 4

Online Booking

$99 - $266
Per Night

$695 - $1861
Per Week

 
           
More Beach and Coastal Locations and Properties