5 Best Osprey Apartments on Holiday Lettings - Villas

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880 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

(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

4

Vacation caravan/mobile home rental

Florida / Osprey

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Air conditioning
Fully furnished trailer, 10 minutes to Siesta Key. Newly updated, all furnished, walking distance to many restaurants and stores. Quiet area, picnic bench next to creek. Wifi, cable all included except electric. New refrigerator and stove. 2 car carport, enclosed Lanai. …see more

from $44 / night

$304 / week

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Responds fast!
avg. 2 hours 6 minutes

from $44 / 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

30

Osprey Vacation condo accommodation

Florida / Osprey

3 6 60 nights min

  • 3 bedrooms
  • Sleeps 6
  • 60 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
This immaculate peaceful vacation property is turnkey furnished and provides 3 bedrooms (beds are king, queen and two twins), office, 2 bathrooms and 2 garage spaces. Secured building with elevator. New furniture, recently painted, high end finishes throughout, no carpe …see more

from $150 / night

$1,050 / week

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from $150 / night

24

Vacation apartment with shared pool in Osprey

Florida / Osprey

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • 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 $89 / night

$623 - $1,120 / week

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Responds fast!
avg. 48 minutes

from $89 / 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 $109 / night

$763 / week

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from $109 / night