Experience the ultimate Caribbean retreat at Windsong, an oceanfront villa with a private beach, expansive pool and patio space. Enjoy snorkeling right off the dock or relax in a hammock under sea grape trees while taking in panoramic views of turquoise waters.
Reviews
9.89.8 out of 10
Exceptional
Entire home
5 bedrooms5 bathroomsSleeps 14307 sq m
Popular amenities
Ocean view
Kitchen
Washing machine
Dryer
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Windsong is an oceanfront, 5 bedroom villa on the pristine northern coast of Grand Cayman a few miles east of the famous Rum Point Beach Club. From a private beach and dock, to expansive pool and patio space, you have everything you could want on your vacation. The renovated interior is comfortable and welcoming, with numerous essentials provided for your stay.
As you pull up to the villa, you'll pass through the horseshoe driveway surrounded by the beautifully landscaped front yard. Windsong, built with a spacious one story floorpan, and no steps to climb, is easily accessible for guests of all ages. Through the front door you immediately notice the panoramic view of the Caribbean waters from the entryway. 10 ft ceilings throughout the villa make the 3300 square feet feel even more spacious. The renovated kitchen is connected to the living/dining areas with an open concept, great for keeping an eye on kids, watching the 60 inch flatscreen TV, or socializing with the family. The windows and sliding glass doors run almost floor to ceiling to expand the beachfront view, but are equipped with custom curtains if you'd like some privacy in the evening. Bedrooms and Baths have recently installed plantation shutters covering all windows.
The large master suite offers a king bed, flat screen TV, and an oceanfront view. The master also contains a comfortable loveseat for watching TV, which can also be converted into an extra twin bed. The fully renovated en suite bath has large custom marble countertops with Jack and Jill sinks, a large shower, as well as a 6 foot oversized soaking tub. Open a bottle of champagne and relax in the bath while you enjoy a show on the TV mounted above the bath.
The second oceanfront suite, on the west side of the villa has a Queen bed and a gorgeous view of the blue Caribbean waters, as well as a new plush mattress and new furniture. It connects to a full private en suite bathroom with marble countertops, as well as a walk in closet.
Also located on the west side of the house, the 3rd bedroom suite has an ocean view, as well as a king bed OR two twin XL beds (set up prior to your arrival upon request), plus a renovated full en suite bath. This room is a great choice for anyone who prefers to sleep in, as the window faces opposite the sunrise, and with the plantation shutters closed it will stay quite dark in the mornings. This room also provides a full crib and changing table, for those traveling with little ones.
The 4th bedroom has recently been renovated and outfitted with new furniture, complete with a dual L-shaped bunk trundle combo (can sleep up to 5, up to 7 with roll away beds for any large parties where all the kids want to sleep together), and multiple arcade games.
Our newest addition to the villa is a second master suite is situated on the southwest corner of the house. The second master has a king bed, large private en suite bath, jack and jill vanity, stand alone soaking tub, and a full rainfall shower.
Windsong also has a 9 seat cinema with vintage theatre seating, and a 87" TV.
Windsong has a full laundry room with a washer, dryer, and utility sink for guests to use during their visit.
Windsong is stocked with almost anything you could need during your stay. The renovated kitchen is well equipped and includes new appliances, plenty of pots, pans, utensils, plates, bowls, glasses, a blender, toaster, cutting knife set, drip coffee pot, and a k-cup coffee maker. Both new bath towels and beach towels are in abundance. All bed linens and pillows are new, and all sheets and pillowcases are Egyptian cotton. All mattresses have been replaced and upgraded recently. You can also enjoy use of our plush robes, stitched with the house logo, yours to keep if you like.
Windsong is equipped with a security system to use if you like, as well as a floor mounted safe to lock your valuables in if needed.
Walk outside and you find an oceanfront saltwater pool, easily big enough for the whole family. Sunbathe poolside, on the extra spacious patio, or feel the warm Caribbean breeze while laying in the hammock hanging under the sea grape trees. Relax in the shade on the covered patio or poolside gazebo. Further down you'll find a white sandy beach, protected by ironshore, as well as a private 75 ft dock that has both a thatch covered gazebo to relax under while enjoying the beautiful Caribbean waters.
Kayaks are provided at the property, and the beach on the west side of the property has a cutout in the ironshore, where the white sand runs into the water, for easy access. We also provide plenty of adult life jackets, kids life jackets of various sizes, as well as puddle jumpers. The beach also has a wood burning fire pit just steps from the ocean.
Some of the best snorkeling on the island can be found right off the Windsong dock. Bring your own snorkel gear or feel free to use the complimentary sets at the house. You will also find various sizes of water shoes for use. The waters along the northern coast are beautiful, but there are patches of turtle grass and some rock/coral formations mixed among the sand, so some prefer to wear footwear.
If you'd like to try fishing during your stay, red snapper, Jack fish, even lobster and conch (in season of course) are regularly caught off the Windsong dock. A grill, which has both propane or charcoal options, is also provided for your use during the stay, and the private beach contains a horseshoe pit for guest use.
Additionally, you will find the property extremely private, with lush landscaping around the yard. However it is still walking distance to a small grocery store, a library, as well as the Northside Post Office.
Windsong has a support team on island should any issues arise. We can also help arrange/refer any reservations, private chefs, in house massages, boat/fishing charters, or excursions you would like to plan in advance. If you have any medical needs or require any special assistance, please let us know and we will be more than happy to help in any way we can.
<<< Included with Windsong >>>
-Bluetooth speaker for use during your stay
-Complimentary coffee K-cups for use in coffee maker.
-Complimentary soap, shampoo, bath products.
-Two plus robes to use during your stay, stitched with the Windsong logo.
-Assistance in setting up anything you need prior to your arrival, including rental cars, airport transportation, reservations, boat charters, excursions, in house chefs, in house massages, recommendations, etc.
-Kayak's, life jackets of all sizes, puddle jumpers, water shoes, snorkel gear, all free to use during your stay.
-4 folding beach chairs (in addition to the more than ample outdoor seating) to set up as you please on your private beach or take with you as you explore the island.
-Crib, changing table, pack-n-play, high chair, among other items that may make the stay more enjoyable for young children.
-Upgraded bed linens including Egyptian cotton sheets and pillowcases.
-In house safe mounted to the floor to lock your valuables in during your stay.
-Security system set up if you wish to use during your stay.
<<< Please Note >>>
-Windsong has been thoroughly inspected and approved by Cayman Islands Department of Tourism. We take pride in having a spotless and well maintained home for you to enjoy during your visit.
-13% Cayman Islands Government Tax is added to all rates, as with any hotel, house, villa or condo in Cayman. This has been reflected in the listed price.
-Windsong requires a $2500, fully refundable, excess cleaning and damage deposit.
-Events/Weddings are permitted but require approval, a small event fee, and security deposit.
-Booking won't be official until the guest rental agreement (sent via docusign) is signed.
Property amenities
Beach
On the beach
Beach loungers
Beach towels
Pool/Spa
Outdoor pool
Private pool
Internet
Available in the house: WiFi
Parking and transport
Car recommended
Parking on site
Kitchen
Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Bedrooms
5 bedrooms
Bedsheets provided
Sofa bed
Bathroom
5 bathrooms
Bathtub
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Living room
Separate dining area
Entertainment
Games
Stereo
TV with cable/satellite channels
Video games
Outdoor areas
Barbecue grill
Firepit
Garden
Outdoor furniture
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
No pets allowed
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Single level property
Smoke-free property
Services and conveniences
Iron/ironing board
Phone
Safe
Location highlights
Near the ocean
Things to do
Kayak
Water sports equipment
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Guest is required to sign rental agreement. Security Deposit of $2,500 is required. Minimum age for primary renter is 25.
Exceeding occupancy limit is grounds for the Owner to immediately terminate the Rental Agreement and cause for immediate evection.
No smoking, no parties, no third-party bookings. Violating house rules may result in additional fines/fees and or eviction.
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
Events allowed
Must have prior approval and additional deposit
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site
Note from host: Must have prior approval and additional deposit
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is recommended for transport to and from this property
About the area
Located in North Side, this holiday home is on the beach. The area's natural beauty can be seen at Grand Cayman Beaches and Seven Mile Beach. Travelling with kids? Consider Queen Elizabeth II Botanic Park and Governor Michael Gore Bird Sanctuary. Visit our North Side travel guide
Does BEACHFRONT w/ Private Dock-50 ft Pool-Theatre have a pool?
Yes, this property has an outdoor pool.
Is BEACHFRONT w/ Private Dock-50 ft Pool-Theatre pet-friendly?
No, pets are not allowed at this property.
How much is parking at BEACHFRONT w/ Private Dock-50 ft Pool-Theatre?
On-site parking is available at the property.
What time is check-in at BEACHFRONT w/ Private Dock-50 ft Pool-Theatre?
Check-in begins at 4:00 PM.
What time is check-out at BEACHFRONT w/ Private Dock-50 ft Pool-Theatre?
Checkout is at 10:00 AM.
Where is BEACHFRONT w/ Private Dock-50 ft Pool-Theatre located?
Nestled on the beach, this North Side holiday home is within a 15-minute walk of Grand Cayman Beaches and North Sound. Mastic Trail North Trailhead and Cayman Crystal Caves are also within 3 miles (5 km).
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BEACHFRONT w/ Private Dock-50 ft Pool-Theatre Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
We had the perfect vacation! The house is well appointed, taken care of, and a lot of little extra touches. The views are incredible and it is a lot of fun to just kayak and snorkel right off the beach.
This property is beautiful. The pool is great. The dock over the water allows fantastic breezes and views. Plenty of room for everyone. Any questions we asked were answered promptly.
This was the perfect property for a large group or family. Beautiful views, every amenity you could ask for and a beautiful home! The northside is very laid-back and quiet with lots of great options around for eating out. Nothing is more than 45 minutes away if you want to go into town to shop or visit seven Mile Beach or any of the other touristy areas. Definitely going to book this one again!
Thank you for allowing our family to stay at your rental home, and for the wonderful care packages. Your rental had everything we hoped for and extra amenities (theatre and arcade games) that made our stay even more enjoyable.
Thanks again for providing our family with cherish memories.
This property is wonderful for families. There were 15 of us. Ages 7-70. Wonderful amenities at the house and great places nearby. We fished, kayaked, had family dinners on the porch, snorkeled, swam and the movie room was great. Let's Bait a Hook a great place to get fishing gear for rent etc. groceries near - expensive but very convenient. The property managers were very responsive and respectful.
Most wonderful home. Exactly as advertised. A delight and a joy. Our multigenerational family found the accommodations perfect for family fun. Can’t say enough about the fabulous features. Wholeheartedly recommend.
Perfect home and off-the-beaten-track location for our family vacation with 9 adults. Snorkeling right off the beach was fantastic. The home is well-stocked with everything needed for cooking and enjoying the amazing Caribbean sea and pool and we appreciated it all! Comfortable rooms & beds. We loved our little curly tailed lizard patio visitor:)
We were fortunate to be able to travel with some friends down to GCM and found the perfect house for us! Well appointed, spacious, breathtaking views. Management had left us some nice welcoming gifts that were used or consumed during the week…very thoughtful. Kitchen was full of everything you would need for cooking and the property was very comfortable. Management was quick to respond to questions that we had and very helpful. Plenty of water toys on property as well.
On the North Shore, within minutes of Rum Point, 20 minutes from Tukka on the West End and 35 minutes from the airport. Ideal swimming, quiet area. Absolutely will return. The villa sleeps plenty. Felt like one week isn’t enough!
Enjoyed the GAZEBO over the water with the nice breezes. We were able to snorkel one day, the weather was not cooperating and most of our stay was cloudy or rainy. We thoroughly enjoyed having the Theatre when the weather was bad. The area was quiet and private which was one of our prerequisite. Enjoyed our boat outing with Crazy Crab and the new Rum Point!
We stayed at this house in 2020 and enjoyed it so much that we stayed again! The location is quiet, the pool and gazebo are wonderful. The house is very comfortable for everyone to spread out and have their own bedrooms and baths. Having a grill, smoker and pizza oven is a real plus if you like to cook with the most perfect view and outside dining area. Grocery and liquor store a short walk down the road. I highly recommend this house for a lovely tropical vacation!
We were 4 adult couples wanting to get away for a week for some fun in the sun. This property was fantastic! We were 6 miles from rum point and all that it has to offer. The pool was clean and inviting. The house was big enough and had all the nexessities. If you are bringing children there is a room with bunk beds in it ... just be aware that there are no drawers or closets in that room. The property manager was amazing. During the eek we had a couple of questions and it took her all of 2 minutes to get back to me each time, and always with the desire to make sure our stay was as seamless and enjoyable as possible!
We had a lovely time at Windsong. The water is steps away from the house. They provided kayaks and water shoes in multiple sizes. You will need water shoes because of the rocks and coral in the water. It has a lovely 30-foot pool with views to the water. The rooms are spacious and the movie room is a bonus. We used the grill outside for a few of our dinners. If you want luxury and tranquility, this place is for you!
This property is located o the North Side so you do need a car. The drive is about 45 min to the seven mile area. Seven mile is very busy so it depends on what type of experience you are looking for. We really enjoyed the private beach, pier, outdoor area. No crowds. Privacy. The set up is great for a family with children as there is a bunk room and theater room to keep them occupied. We enjoyed visits from the local roosters and friends. The only negative is there was a mildew smell at times but it is the islands!!
Amazing property and location. Large pool you can do laps in, kayaks and other equipment, and snorkeling with lots of fish and interesting rock formations right off the beach. A gazebo at the end of the dock that it great for relaxing, enjoying the sea breeze, and kicking back and reading a book. Away from the traffic and hustle and bustle but close to activities at Rum Point.
The property needs a bit of TLC though, signs there was a roof leak in the past that hasn't been fully restored, dirty windows marring the beautiful view, rusted outdoor pizza oven and BBQs, and signs of age all around.
Overall excellent because anyone would enjoy the stay, but the property has the potential to be perfect.
Six girlfriends who have known each other over 50 years chose Windsong as our biennial trip and weren’t disappointed! The house was perfect with nice bedrooms and bathrooms. The kitchen was well stocked as we cooked most of our meals at home. The dining table was perfect for evening game nights. The pool area was beautiful - with lots of chairs, clean/warm pool and amazing views. A couple of us ventured on the kayaks and snorkeling from the beach in front of the house - it was very windy so it was a bit difficult but still fun. We had a rainy day so even took advantage of the theater. We did a couple of adventure days to Seven Mile Beach, Rum Point and Starfish Point. We loved the grocery store Chisholms that was walking distance - they had a surprising inventory including a liquor store. The communication with the house management was always professional and immediate. We have traveled as a group for the past 14 years and this was voted the best vacation so far.
We just got back from a week at this house. We were a group of 7 with ages ranging from 3 to 70. There was something for everyone. The house was laid out perfect. I can honestly say this was the best vacation experience my family has had together, and it rained for 4 days. They have thought of everything; swim stuff for the kids, all the bedding needs for kids, fishing equipment, snorkle gear, kayaks...the list goes on.
We had a "situation" with the air conditioner around day 4. It stopped working in the back 3 bedrooms. We didnt realize it until it was time for bed. We started talking about who was going to sleep where since the AC was out. I reached out to the owner around 8:30 pm. I figured she would tell me they would be out in the morning. Would you believe, she had a technician out at the house within 30 minutes and he had it fixed before 9:30. Things happen, but this level of service was unbelievably good. There is a strong chance we will be back next year. 5 STARS FROM OUR FAMILY!!!
Wonderful family vacation! The house and location were beautiful. We really enjoyed the pool and swimming and kayaking in the ocean right out the back door. The gazebo at the end of the dock was a great place to relax!
Very nice property. Easy swim out to reef to snorkel. Need water shoes as waterfront is more rocky. Great layout for 4 couples. Two nice beach clubs (kaibo and rum point) with good restaurants 10 minutes away. Not as touristy as seven mile beach. Would go back!
My husband and I took our children and grandchildren to the Caymen Islands for Spring Break and stayed in this wonderful home. For our family the house worked out so well. There was plenty of space, we enjoyed the pool, the Gazebo, the kayaks, and all the extras. The location was great for what we wanted to do - Rum Point, Sting Ray City, Starfish Point, Crystal Caves were all pretty close by and the ability to walk to the convenince store was fantastic. Thank you for a place that our family could enjoy so well and create such wonderful memories.
This was one of our best vacations yet. I have been gifting my family with a surprise family vacation for christmas for 10 years instead of stuff.The house was great. It was well stocked, we needed nothing. Location? Perfect. The kids loved the pool and the kayaks and the fire pit where we did the s'mores that were in a basket for us upon arrival. Management was one of the best we have dealt with. We will be back for sure.