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Compare 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.
9.2 out of 10, Wonderful, (9)
"Flew into ELH airport. House was 1.5 hour drive from airport. Roads are rough, lots of potholes, speed bumps are hard to see. Stopped at supermarket in Governor's Harbor to get supplies before going to house. Arrived at house 4pm, everything was unlocked so we just went in, put on bathing suits and went straight to the beach in front of house. Water was beautiful and warm. 4 bedrooms each with own bathroom. 1 bedroom off main great-room, other 3 bedrooms are off the pool area. All bedrooms have...
Luxurious Beachfront Estate w/Pool on Windermere. Club, Tennis, Pickleball.
Private family beach bungalow - on a beautiful swimming beach
10.0 out of 10, Exceptional, (91)
"We loved this house and especially the screened in porch were we spent every morning and evening. Well stocked kitchen with everything we needed. We were six adults and 2 kids under 6 and we had a fantastic time. Thank you Charles for making it easy and a very relaxing stay."
Private family beach bungalow - on a beautiful swimming beach
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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, (4)
"We had such a great time and amazing, relaxing and private vacation here. Can’t wait to come back"
Private Beachfront Estate Home w/Pool on Gated Windermere Club Membership
FOR RENT BY LOCAL LADY 2 BEDROOMS TWO BATH CLEAN AIR CONDITIONED BAHAMIAN HOME
9.8 out of 10, Exceptional, (8)
"House was good and quiet. Only hear the birds in the morning. Dirt road in is rough and traveled only by those who live there, which is good. Stephanie was a good host - responsive to my questions and provided easy check in and out. I’d stay there again, no question."
FOR RENT BY LOCAL LADY 2 BEDROOMS TWO BATH CLEAN AIR CONDITIONED BAHAMIAN HOME
Lux New Windermere Home w/Pool, Boat Dock, Beach Access, Club Membership
9.8 out of 10, Exceptional, (7)
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.
Old Mizp - A Charming Escape
Old Mizp - A Charming Escape
Halcyon House 3 Bedroom Home
3.0 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
Savannah House by Eleuthera Vacation Rentals
3.5 star property
Savannah House by Eleuthera Vacation Rentals
Provender 5 Bedroom Home
3.0 star property
Provender 5 Bedroom Home
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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.

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.

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