Search Vacation Homes in Greencastle

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 26 Vacation Homes in Greencastle with updated reviews, rates, and availability.

Beach Front Private Home with Dock

9.4 out of 10, Exceptional, (28)
"Better than the pictures can display. Everything we needed right there. Beach, shells, space, privacy, very comfortable bed and furnishings. Nice hot showers, great kitchen, beautiful porch , perfect for kayaking. I could live here full time ❤️❤️❤️"
Beach Front Private Home with Dock

Luxurious Beachfront Estate w/Pool on Windermere. Club, Tennis, Pickleball.

9.0 out of 10, Wonderful, (10)
"The property itself was run down and dirty. The location was great."
Luxurious Beachfront Estate w/Pool on Windermere. Club, Tennis, Pickleball.

ULTRA LUX Coconut Cove Compound! 2.5 acres with 300 ft PINK SAND BEACH

10.0 out of 10, Exceptional, (1)
"Unfortunately for us there was a hurricane stirring up in the Bahamas during our visit in mid October. The storm created lots of wind and seaweed along the shore in front of the property. Although his workers tried to clean up the beach it was impossible to stop the seaweed from covering the beach. Chris informed us of a back road that took us to some calmer waters where we were able to spend some fun water time. "
ULTRA LUX Coconut Cove Compound! 2.5 acres with 300 ft PINK SAND BEACH

Private family beach bungalow - on a beautiful swimming beach

10.0 out of 10, Exceptional, (98)
"We stayed at Parlay at Sunset 11/12-11/17. The home is huge and beautiful! I was almost sad we had such a large space for 3 people... almost! The yard and beach are gorgeous!We never saw anyone else on the "private" beach. Charles made sure we were well taken care of and even brought us homemade punch and rum! We will be back!!"
Private family beach bungalow - on a beautiful swimming beach

Historic Home Directly on Windermere Beach w/Club, Pool, Pickleball, Tennis

9.6 out of 10, Exceptional, (46)
"Perfect location, beautiful beach, excellent food nearby at the club and super-helpful staff. The house isn't new or shiny, if that's what you're looking for, but it worked well for us. We had a great week and can't wait to go again. Thank you to everyone there!"
Historic Home Directly on Windermere Beach w/Club, Pool, Pickleball, Tennis

AS SEEN ON BAHAMAS LIFE! Newly Remodeled Windermere Beach House w/ Pool, Club

9.8 out of 10, Exceptional, (18)
"Wonderful house and location. Loved every minute of our stay ."
AS SEEN ON BAHAMAS LIFE! Newly Remodeled Windermere Beach House w/ Pool, Club

Private Villa Directly on Windermere Beach, Private Pool, Tennis

10.0 out of 10, Exceptional, (3)
"Family of 6, kids ages 18-26. House and beach were incredible. Best beach in the world! Host extremely responsive to all requests. Access to club house and pickleball and Gym a big plus. 100% would stay again!!"
Private Villa Directly on Windermere Beach, Private Pool, Tennis

Private Beachfront Estate Home w/Pool on Gated Windermere Club Membership

10.0 out of 10, Exceptional, (5)
"I first want to say I never wanted to leave, Eleuthera is an amazing island and something very special. If you want a secluded house with a private beach to enjoy the views of the ocean, this is the place. The blue water views when you walk in are amazing and the property offers so much! The house is beautiful plenty of room for a family, the kitchen is well equipped with everything you need, best past is an amazing ice maker we used excessively! There are three different types of coffee makers,...
Private Beachfront Estate Home w/Pool on Gated Windermere Club Membership

Lux New Windermere Home w/Pool, Boat Dock, Beach Access, Club Membership

9.8 out of 10, Exceptional, (8)
Lux New Windermere Home w/Pool, Boat Dock, Beach Access, Club Membership

Stunning Private Beachfront Estate on Pink-Sand Cotton Bay Beach

10.0 out of 10, Exceptional, (2)
"We had a wonderful time at Rock Hill House. The house and beach are both stunning and in a peaceful part of south Eleuthera. Really appreciated that every bedroom had its own bathroom - it made for excellent privacy for all the guests. The beach is lovely fine sand and there is pretty decent offshore snorkeling - we saw the largest parrot fish that we have EVER seen and we are long time snorkelers. Bring your gear! The tug and barge wrecks just offshore are really cool and remind you of the...
Stunning Private Beachfront Estate on Pink-Sand Cotton Bay Beach

Your private get away hidden in historic island settlements

Your private get away hidden in historic island settlements

Tara Estates tucked away on a private property.

10.0 out of 10, Exceptional, (1)
"Tara Estate worked well for us as we primarily came to fish out of Davis Harbor, which is relatively close by. The house had a few “quirks”, but they were expected as it is nearing 90 years old. However, the property managers, a Shorlette and Joey, were amazing and made sure we were comfortable and satisfied. Thanks for a great two weeks in Tara Estate!"
Tara Estates tucked away on a private property.

Villa De La Rose - A Stylish Escape! Enjoy sunset dinners.

Villa De La Rose - A Stylish Escape! Enjoy sunset dinners.

House of Love - Perfect Vacation Spot

2.0 star property
House of Love - Perfect Vacation Spot

The Bahamian Farm House

The Bahamian Farm House

Old Mizp - A Charming Escape

Old Mizp - A Charming Escape

Halcyon House 3 Bedroom Home

2.5 star property
Halcyon House 3 Bedroom Home

Sand Dollar Cottage by Eleuthera Vacation Rentals

4.0 star property
10.0 out of 10, Exceptional, (3)
"Excellent stay. Great location."
Sand Dollar Cottage by Eleuthera Vacation Rentals

Palm Hill House 4 Bedroom Home

2.0 star property
Palm Hill House 4 Bedroom Home

Utopia House 3 Bedroom Home

3.0 star property
Utopia House 3 Bedroom Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Greencastle
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Greencastle

Stunning Private Beachfront Estate on Pink-Sand Cotton Bay Beach

10.0 out of 10, Exceptional, (2)
"We had a wonderful time at Rock Hill House. The house and beach are both stunning and in a peaceful part of south Eleuthera. Really appreciated that every bedroom had its own bathroom - it made for excellent privacy for all the guests. The beach is lovely fine sand and there is pretty decent offshore snorkeling - we saw the largest parrot fish that we have EVER seen and we are long time snorkelers. Bring your gear! The tug and barge wrecks just offshore are really cool and remind you of the...
Stunning Private Beachfront Estate on Pink-Sand Cotton Bay Beach

Your private get away hidden in historic island settlements

Your private get away hidden in historic island settlements

Palm Hill House 4 Bedroom Home

2.0 star property
Palm Hill House 4 Bedroom Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.