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Compare 30 Vacation Homes in Greencastle with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (4)
"The property was spectacular with great areas for hanging out and especially with amazing speakers everywhere on the property. Also with a plenty of kayaks we were able to take bigger groups out to the reef right in the bay. We will definitely visit again. "
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, (104)
"The property was so beautiful and made you never want to leave! We enjoyed snorkeling in the crystal clear water right outside the backdoor and stargazing under the clear starlit sky while listening to the waves crash just feet from us. We could not have asked for a more peaceful and serene place to be! Diana the owner and Charles the property manager were so kind and helpful the entire trip from start to finish which made a perfect experience even better than we could have ever imagined. We...
Private family beach bungalow - on a beautiful swimming beach

House of Love - Perfect Vacation Spot

2.0 star property
6.0 out of 10, (1)
"Our 4 night stay was okay but could have been much better with a bit more attention to both the house itself and to the communication.Upon arrival, the power was out. We’re familiar with power outages on island but without WiFi and sketchy cell service in the area, we had to drive 20 minutes down the road to inquire about the outage. We learned from the host- we never did get a response from the property manager- that there was a scheduled power outage that day and power would be back on in a...
House of Love - Perfect Vacation Spot

As seen on Bahamas Life! Newly Remodeled Windermere Beach House w/ Pool, Club

9.8 out of 10, Exceptional, (19)
"Wonderful house and location. Loved every minute of our stay ."
As seen on Bahamas Life! Newly Remodeled Windermere Beach House w/ Pool, Club

Historic Home Directly on Windermere Beach w/Club

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

Private Villa Directly on Windermere Beach, Private Pool, Tennis

10.0 out of 10, Exceptional, (4)
"Had a wonderful time, beautiful property and owner was very responsive throughout the stay, highly recommend"
Private Villa Directly on Windermere Beach, Private Pool, Tennis

Stunning Private Beachfront Estate on Beach

10.0 out of 10, Exceptional, (3)
"My family and I had a wonderful vacation while staying at Palm Hill. The beach in front of the house is pristine, private and all around just stunning. Cotton Bay itself offers a unique opportunity to experience Eleuthera, from the access to the huge private beach, the lagoon in the back, easy snorkeling grounds and quite nature. Highly recommend. "
Stunning Private Beachfront Estate on Beach

Beach Front Private Home with Dock

9.4 out of 10, Exceptional, (28)
"Great stay with the family in Tarpon Bay. Hosts took great care. We will be back for sure 😊"
Beach Front Private Home with Dock

The Bahamian Farm House

10.0 out of 10, Exceptional, (1)
"Eleuthera means freedom, and free we felt. Atop a little hill sits the Bahamian farm house, tucked away by native bush and trees. The house fills with warm light and cool breeze. It is true and pure island living in the best say. "
The Bahamian Farm House

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

10.0 out of 10, Exceptional, (5)
"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

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

9.4 out of 10, Exceptional, (10)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Pointe House was a lovely place to stay."
Lux New Windermere Home w/Pool, Boat Dock, Beach Access, Club Membership

Your private get away hidden in historic island settlements

Your private get away hidden in historic island settlements

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

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

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.

Utopia House 3 Bedroom Home

3.0 star property
Utopia House 3 Bedroom Home

Old Mizp - A Charming Escape

Old Mizp - A Charming Escape

Palm Hill House 4 Bedroom Home

2.0 star property
Palm Hill House 4 Bedroom Home

Coriolana 4 Bedroom Home

3.0 star property
Coriolana 4 Bedroom Home

Halcyon House 3 Bedroom Home

2.5 star property
Halcyon House 3 Bedroom Home

Provender 5 Bedroom Home

3.0 star property
Provender 5 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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Other property types in Greencastle

Stunning Private Beachfront Estate on Beach

10.0 out of 10, Exceptional, (3)
"My family and I had a wonderful vacation while staying at Palm Hill. The beach in front of the house is pristine, private and all around just stunning. Cotton Bay itself offers a unique opportunity to experience Eleuthera, from the access to the huge private beach, the lagoon in the back, easy snorkeling grounds and quite nature. Highly recommend. "
Stunning Private Beachfront Estate on 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.