Castle In Hawaii - Vacation Rentals in Osprey Point

MARSH/SUNSET VIEWS-DOCK/POOL-RENOVATED From US $254
         

10.0 (149 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Seascape 3559 From US $217
         

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New
Villa
  • Air Conditioner
  • Parking
  • View
The Sanctuary at Kiawah Island Golf Resort From US $836
         

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9.6 (243 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Windswept Woodlands 4334 From US $100
         

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8.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Dunlin, Auberge Collection From US $800
         

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9.6 (40 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Courtside 1607 From US $97
         

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7.7 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Oceanfront Renovated Mariners Watch From US $1,530
         

9.8 (98 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Oceanfront Retreat for Two Couples From US $1,385
         

9.8 (50 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Spectacular Panoramic Marsh Views! Amenity access included! From US $422
         

Coastal Calm- Luxury in the Lowcountry From US $609
         

Beautiful reno, central, to beach and golf From US $655
         

9.6 (23 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated, central, in popular location From US $540
         

Picturesque View in Parkside! 2bd/2ba From US $366
         

9.2 (44 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osprey Point.

Weather in Osprey Point

View the weather forecast for Osprey Point before booking your Osprey Point Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Osprey Point Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Osprey Point?
How many vacation rentals are available in Osprey Point?

Currently, the total number of properties listed in 2026 is over 528 in the Osprey Point area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osprey Point.