27 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Homes
Villas
Barns
Boats
Cabins
Castles
Chalets
Cottages
Estates
Farmhouses
Hotels
Lodges
Studios
Townhomes
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

27 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Osprey Vacation Rentals with Online Payment(27)

27 Results
$595 - $1,095
per week
4 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night min stay
(16)
$1,500 - $3,500
per month
90 - 180 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
90 - 180 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
14 night min stay
(8)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night min stay
$3,800
per month
28 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
28 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 - 30 night min stay
(15)
$2,500 - $3,900
per week
7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
$3,600
per month
30 - 90 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
30 - 90 night min stay
$1,500
per month
27 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
27 - 30 night min stay
$484 - $1,750
per week
4 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 30 night min stay
2 Reviews
$933 - $1,500
per week
7 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(6)
  • Studio,
  • 1 BA,
  • Sleeps 4
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
29 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
6 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
14 - 30 night min stay
2 Reviews
  • 1 BR,
  • 2 BA,
  • Sleeps 4
$2,200 - $2,300
per month
30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night min stay
$2,500 - $4,500
per month
29 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
29 - 30 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 - 30 night min stay
(3)
  • Studio,
  • 1 BA,
  • Sleeps 4
1 - 4 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
90 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 5
90 night min stay
$2,200 - $4,100
per month
29 - 90 night min stay
  • Studio,
  • 2 BA,
  • Sleeps 6
29 - 90 night min stay
 View map Map
Advertisement
 

Recent Osprey Reviews

1st long vacation - won't be last!

5 of 5
My husband just retired and we were looking for a place on short notice. We were so lucky to find Breda and PJ's villa as our first experience! The house and pool are fabulous. The quiet neighborhood and surroundings are beautiful and we were completely relaxed during our 3 week stay. The local restaurants were delightful and we visited Siesta Key Beach. Most days were spent lounging by the pool and just relishing in the beautiful weather! I am grateful to Breda and PJ for helping to make Bob's first retirement vacation perfect!
  • Submitted: Jan 3, 2015
  • Stayed: Dec 2014

Great Beach Getaway

5 of 5
We enjoyed our stay at this house on Casey Key. It has a very natural, heavily-landscaped yard, which gives privacy from some of the less naturally inclined neighbors - besides being on a wonderful beach, of course. The furniture is less than perfect, but we found that putting away some of the "extra touches" that the maids put out really improved the looks of the place. It could use some neatening up, however, with so many books just thrown up on the shelves etc. So all in all, I recommend this house but with the warning not to expect elegance, just a very nice relaxing visit.
  • Submitted: Dec 27, 2007
  • Stayed: Aug 2007