5 Best Osprey Apartments on Holiday Lettings - Villas

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1,155 Vacation rentals

(1) Excellent 

17

Vacation home in Osprey

Florida / Osprey

3 8 90 nights min

  • 3 bedrooms
  • sleeps 8
  • 90 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
New on the market! Magnificent big villa, 3 bedrooms, 2.5 bathrooms, dining room, leaving room and family room. Freshly paint with new furniture.Plenty lanai room with swimming pool.The house is quite equipped to receive easily 6 people. Placed well close of many beac …see more

from $171 / night

$1,197 / week

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from $171 / night

29

Villa accommodation in Osprey with golf nearby

Florida / Osprey

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 7 mi
  • Swimming pool
  • Child friendly
Dear Renter, I am Beya, the owner and I'm offering authentic villas in the natural environment on Palmer Ranch. The villa is a spacious house with stunning garden with palm and pine trees. The location is just perfect, Mall, restaurants, and park are located just minute …see more

from $99 / night

$654 - $794 / week

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from $99 / night

24

Vacation apartment in Osprey

Florida / Osprey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo that sleeps 4 in Siesta Key. This coastal condo boasts all the amenities of home with the luxuries of an upscale resort. Spend your days lounging around the heated community pool or take …see more

from $142 / night

$994 / week

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avg. 19 minutes

from $142 / night

(2) Very Good 

17

Vacation home in Osprey

Florida / Osprey

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Absolutely the best value for your vacation dollar in the Sarasota-Osprey-Nokomis-Venice area ! This newly renovated pet friendly paradise is a single family 3 br - 2 bath home with heated pool that has it all. Large, extremely well equipped kitchen with granite counte …see more

from $175 / night

$1,100 / week

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from $175 / night

18

Vacation condo in Osprey

Florida / Osprey

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Child friendly
Sunrise Cove Yacht & Racquet Club is the most scenic, relaxing vacation spot on Siesta Key, a barrier island separating the Gulf of Mexico from Sarasota Bay. Located at the quiet end of Siesta Key, across from Turtle Beach, every unit has a direct water view. Nearby Sie …see more

from $68 / night

$476 / week

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from $68 / night

(2) Excellent 

15

Vacation condo with golf nearby in Osprey

Florida / Osprey

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stoneybrook Golf & Country Club is a gated community on Palmer Ranch with a fully renovated clubhouse with fine and casual dining, close proximity to Siesta Key's world-famous beaches, shops, restaurants, and Sarasota's active arts communities. This unit is a ground-flo …see more

from $60 / night

$420 / week

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from $60 / night