Entire home

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Escape to your own tropical haven where turquoise waters meet powdery white sand beaches. Relax by the oceanfront pool or unwind on your private beach with stunning sunsets.

Photo gallery for BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

On the beach, sun loungers, beach towels
Fridge, microwave, oven, stovetop
Outdoor pool
On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 14307 sq m

Popular amenities

  • Parking available
  • Washer
  • Barbecue grill
  • Air conditioning
  • Kitchen

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 manager

Arcadian Avenue

Languages

English

Property amenities

Beach

  • On the beach
  • Beach towels
  • Beach sun loungers

Pool/Spa

  • Private pool
  • Outdoor pool

Internet

  • WiFi available

Parking and transportation

  • Onsite parking
  • Car recommended

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee grinder
  • Paper towels
  • Coffee/tea maker
  • Spices

Bedrooms

  • 5 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Toilet paper
  • Soap
  • Towels provided

Living spaces

  • Living room
  • Dining room

Entertainment

  • TV with cable/satellite service
  • Video games
  • Games
  • Stereo

Outdoor areas

  • Patio
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Safe
  • Iron/ironing board
  • Phone

Location highlights

  • Near the ocean

Things to do

  • Water sports equipment
  • Kayak on site

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 3300 sq ft (307 sq m)

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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 transportation to and from this property

Property is also known as

Windsong Renovated Beachfront w/ Private Dock 50 ft Pool
Windsong Renovated Beachfront w/ Private Dock 50 ft Pool Villa
Windsong Renovated Villa
Windsong Renovated Beachfront w/ Private Dock 50 ft Pool
Windsong Renovated
WINDSONG - Beachfront w/ Private Dock & 50 ft Pool Villa
WINDSONG - Beachfront w/ Private Dock & 50 ft Pool North Side
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Windsong Renovated Beachfront w/ Private Dock 50 ft Pool
Windsong Renovated Beachfront w/ Private Dock + 50 ft Pool Villa

About the neighborhood

Map
Northside

What's nearby

  • Grand Cayman Beaches - 6 min walk
  • Mastic Trail North Trailhead - 5 min drive
  • Cayman Kai Public Beach - 8 min drive
  • Rum Point Beach - 9 min drive
  • Starfish Beach - 13 min drive

Getting around

  • Owen Roberts Intl. Airport (GCM) - 41 min drive

Restaurants

  • ‪Kaibo restaurant . beach bar . marina - ‬12 min drive
  • ‪Rum Point Club and Restaurant - ‬10 min drive
  • ‪Kaibo - ‬12 min drive
  • ‪Czech Inn Grill - ‬18 min drive
  • ‪Grapetree Cafe - ‬20 min drive

Frequently asked questions

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.

What time is check-in at BEACHFRONT w/ Private Dock-50 ft Pool-Theatre?

Check-in begins at 4:00 PM.

Where is BEACHFRONT w/ Private Dock-50 ft Pool-Theatre located?

Nestled on the beach, this North Side vacation home is within a 10-minute walk of Grand Cayman Beaches and North Sound. Mastic Trail North Trailhead is 1.9 mi (3.1 km) away.

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BEACHFRONT w/ Private Dock-50 ft Pool-Theatre Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 57 out of 61 reviews
Rating 8 - Good. 4 out of 61 reviews
Rating 6 - Okay. 0 out of 61 reviews
Rating 4 - Poor. 0 out of 61 reviews
Rating 2 - Terrible. 0 out of 61 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Eric E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Windsong Wonderful
What a great place for 3-4 couples or a big family. Close to awesome restaurants, Rum Point but away from crowds!
Stayed 7 nights in Feb 2024

10/10 Excellent

Keri G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Rarely gets better than this
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:)
Stayed 7 nights in May 2024

8/10 Good

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great villa beach too much coral
Great villa. Beach too much coral
Stayed 7 nights in Feb 2024

10/10 Excellent

Sheryl M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
This property was amazing. Everything was exactly as described. We will stay here again.
Stayed 7 nights in Apr 2023

10/10 Excellent

Conrad S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great time on North Side
Great house and location on the North Side of Grand Cayman!
Stayed 7 nights in Dec 2019

10/10 Excellent

Jay R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome Family Vacation
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.
Stayed 7 nights in Aug 2023

10/10 Excellent

Ann W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous
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!
Stayed 7 nights in Feb 2024

10/10 Excellent

Sandra M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we expected and more!
Perfect fit for our three generation family.
Stayed 7 nights in Jun 2022

8/10 Good

Patricia B.

Liked: Cleanliness, communication, location, listing accuracy
Property
The house was in somewhat good repair. Two of the bedrooms were small and no closets. Otherwise the house was good for 7 people.
Stayed 7 nights in Jan 2024

10/10 Excellent

Ben B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Windsong is incredible!
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!
Stayed 7 nights in Oct 2023

10/10 Excellent

Valerie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
We had the best time at this home. So much room and clean. We swam daily and watched Movies in the most awesome theater room. We were able to kayak and snorkel from the property and enjoy game night. We loved this place. Recommend it and would absolutely come back.
Stayed 7 nights in Apr 2023

10/10 Excellent

Shawn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great getaway in Grand Cayman
We stayed here with 14 people, 4 families with kids. The house was amazing as each room had its own bathroom. Kitchen, living room, patio, pool, pier/dock were perfect for our stay. The kids loved the bunk room with video games and the cinema room. The driveway accommodated our 3 cars easily. I'd stay here again in a heart beat.
Stayed 7 nights in Jan 2023

10/10 Excellent

John Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise at Your Doorstep
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.
Stayed 7 nights in Mar 2024

10/10 Excellent

Denise V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Windsong
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!
Stayed 7 nights in Mar 2024

10/10 Excellent

Benjamin J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot
A truly great spot and wonderful experience. The property is located within a short driving distance to run point, Kaibo, and Tukka restaurants. A small grociery/convenience store was within walking distance. The house accommodated nine of us with room to spare. The dock with the gazebo was a great place to watch the sunset, and during the day we could enjoy the pool or swim a very short distance out to a beautiful reef.
Stayed 7 nights in Apr 2023

10/10 Excellent

Thomas B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
We have stayed in a number of homes on the Cayman island. This was one of the best! The location was remote and quiet. The house was well appointed and there was something for everyone. The home theatre and arcade games were a big hit with the kids in the evening. The reefs in front of the house were superb for fishing, snorkeling and ocean kayaking. The pool was great for those who chose not to go into the ocean. Would definitely return!
Stayed 7 nights in Jan 2023

10/10 Excellent

Randy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just Perfect
We Anticipated this trip from NJ, MD, and DE FOR about 6 mos. and it was absolutely perfect for us. The house is ready for everything that you would want to do. We had a chef, we made our own pizza dough and cooked them beautifully in the pizza oven by the pool. We fished from “our own” pier and gazebo, snorkeled off the private beach, kayaked and watched movies in the theater. This house was made for us. We had a 3yo, 6yo, 11yo and a 14yo and 6 adults and we were never bored. This is as advertised. We will come again for sure.
Stayed 7 nights in Jun 2023

10/10 Excellent

Kurt T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Family Vacation
We celebrated our 15th anniversary (we were married on Grand Cayman) and my wife's 50th birthday with friends and family here. We normally stay at hotels on 7 mile beach, but wanted a house where we (12 people total) could be together. This place was a perfect hideaway from the hustle and bustle of 7 mile beach. It was exceptionally clean, beautiful and spacious. The kids and adults enjoyed the pool every day from sunrise to sunset but our favorite spot was the gazebo on the dock which was shaded and always had a breeze. Snorkeling off the beach (including a night snorkel) was enjoyed by all as there was abundant sea life. We rented a car and purchased fresh fish from local fishermen and grilled it at night. The views of the ocean, especially sunset, were amazing every day. If you're looking for a great place to gather a large group in a quiet, private setting, look no further.
Stayed 7 nights in Jun 2023

10/10 Excellent

sally d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous!!
This is a beautiful house. Spacious, clean, terrific amenities and the backyard is like being in a resort. The "movie room" (as my grandsons called it :) ) and the video games were huge hits with them. If you want to make a meal, the kitchen is well stocked with pots, pans etc. Extra refrgerator for you drinks. The bedrooms are a good size and all (except the bunk room) were en suites. The house is located on the North side where it is really quiet. The house is surrounded with lush greenery and is very private. The gazebo over the water is a great place to watch the sunrise. We had some issues with the TV and ice machine but Megan took care of them. Megan is phenomenal!! I would highly reccomend choosing this rental
Stayed 7 nights in Apr 2023

10/10 Excellent

Cheryl K., Swarthmore, PA

Liked: Cleanliness, check-in, communication, location, listing accuracy
A magical week on the water
Megan was so helpful to work with, both before and during our stay. I can't say enough wonderful things about her.. There were some initial issues (king bed wasn't set up; not enough towels), but the management company took care of everything right away. Property is showing signs of wear a little bit--the dishwasher is *really* loud (especially during the first hour--we thought maybe it was broken, but it did the job); windows stuck shut from the weather; many of outdoor solar lights and pool lights don't work--but nothing that really took away from our overall enjoyment of the place. Appreciated all that was available for guest use--kayaks, water shoes, snorkel gear. I spent many happy hours of vacation sitting under the gazebo, soaking in the Caribbean sounds and breezes. Loved the relative privacy of this part of the island as well as the ability to walk to Chisolm's for groceries and the Island Jerk for some AMAZING jerk chicken. Hope to return one day!
Stayed 7 nights in Dec 2019

8/10 Good

Kathy C.

Liked: Cleanliness, check-in, communication, listing accuracy
Family Spring Break 2023
Things ran very well and communication with Megan was excellent both before and during our stay. It would be nice to have more melamine or plastic dishes and glasses. We searched for firewood at numerous grocery stores for the fire pit as suggested but did not find any. We did purchase some “wood charcoal” but weren’t able to try it due to weather. We had 6 children ages 1-9 who loved the pool and movie theater! It was good to have 2 great washers and dryers. They got much use as did the dishwasher. This is a great house but quite far from some activities we wanted to do. Star Fish Point was close and a great beach and calm water for little ones, It will be nice when construction at Rum Point is complete and more options for dining and activities are available in this location.
Stayed 7 nights in Mar 2023

10/10 Excellent

Curtis M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great quiet location
None of this would knock the property from a five star rating IMO, but they are worth mentioning. Taking all into consideration, the price is a bit on the high side. -2nd “master bedroom” is extremely small. We split the house and to be polite took the 2nd “master suite”. The bathroom was nice when the cabinet doors weren’t falling off. No ocean view and barely room to walk around the bed. -In fact there are only ocean views from 2 of 5 rooms and those are not great views. Standing with your face on the glass to see the water isn’t an ocean view. -The bunk bed room has no dresser. What do you do with 4 kids’ clothes that sleep in that room? -Theatre has no surround sound. -90% of snorkel gear broken. -No wood for fire pit. -Missing horse shoes. -No sandy beach for kids. -Strangers fishing from private pier our first night. “We were asked to have them leave”. -Provided Bluetooth speaker barely audible. -Except for Chisholm's convenience store, it’s a 15 minute drive anywhere. -Primary microwave broken. -Only one working fishing pole with line and no tackle on premises. Again these things seem petty, however they are all mentioned in the advertisement for the property, and all fell short. We were a little disappointed we didn’t get to have a fire or fish because we didn’t care to go on a mission for wood or tackle. I did call about the men on our dock, and the response was immediate. Although, the answer was no exactly what we hoped for. Could use some TLC by ownership to list in this price range
Stayed 7 nights in Mar 2023

10/10 Excellent

Lindsey Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Aug 2024

10/10 Excellent

Sam L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise perfection
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.
Stayed 7 nights in Aug 2024

10/10 Excellent

ashley b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was perfect
Stayed 7 nights in Feb 2024