House in Cruz Bay
4 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
This air conditioned house has 2 bedrooms and 2 full bathrooms, each on a different level, giving maximum privacy for couples or a family of four. Enjoy a peaceful, private and perfect vacation at our home in Chocolate Hole, a tropical paradise escape at an affordable price point. Staying close to Cruz Bay makes the home an ideal location to enjoy all that St. John has to offer, while also feeling at home in your own, exclusive setting.
The bedroom on the air conditioned main level has a queen size bed, TV, and a full bath with shower, as well as ceiling fans. The bedroom on the air conditioned lower level has twin beds or a converted king size bed, TV, a full bath with shower, sitting area, a deck and A/C -- though the relaxing trade winds and Christmas breezes, for which the home is named, make it comfortable without. This lower level has its own entrance and is approached by an outside staircase.
The house is a quick 10 minute drive (a little over a mile) to the center of Cruz Bay, 8 minutes to grocery stores, and 15 minutes to the pristine, white sand beaches of the North Shore.
Guests especially enjoy kicking back after a day at the beach to experience St. John’s magnificent sunsets -- perhaps even glimpse the elusive green flash as the sun sinks into the Caribbean Sea -- from the lounge chairs or table on our expansive double deck, which faces southwest toward Chocolate Hole, Rendezvous Bay and the island of St. Croix. The water views are breathtaking!
After taking it all in, easily prepare and eat your own meal in our fully equipped kitchen and dining area (or outdoor gas grill), then relax further in the living room -- which has a flat-screen smart Netflix enabled television, cable, Wi-Fi wireless internet and DVD player -- or simply unplug and unwind to the natural symphony of the forest, as cooling breezes rustle the surrounding canopy outside. We even have a small library of beach reads for your enjoyment. Ahhh... blissful!
Christmas Winds as a whole is a well-maintained wood home with ceramic tile floors, native stonework and high ceilings. The atmosphere in the house is informal, and the home is ideal for one or two couples, or a relaxing honeymoon. The home is also good for a family with older children who can sleep on a separate level from parents. There is no maid service, but it is thoroughly prepared for guests and cleaned upon departure, and our house manager is happily on call for any questions. There are linens, beach and bath towels and a full laundry with washer and dryer, as well as beach chairs and some beach accessories and pool toys for guest use (snorkel fins and masks, boogie board, etc.).
Do feel free to email with any questions. We hope to see you soon on St. John!
The bedroom on the air conditioned main level has a queen size bed, TV, and a full bath with shower, as well as ceiling fans. The bedroom on the air conditioned lower level has twin beds or a converted king size bed, TV, a full bath with shower, sitting area, a deck and A/C -- though the relaxing trade winds and Christmas breezes, for which the home is named, make it comfortable without. This lower level has its own entrance and is approached by an outside staircase.
The house is a quick 10 minute drive (a little over a mile) to the center of Cruz Bay, 8 minutes to grocery stores, and 15 minutes to the pristine, white sand beaches of the North Shore.
Guests especially enjoy kicking back after a day at the beach to experience St. John’s magnificent sunsets -- perhaps even glimpse the elusive green flash as the sun sinks into the Caribbean Sea -- from the lounge chairs or table on our expansive double deck, which faces southwest toward Chocolate Hole, Rendezvous Bay and the island of St. Croix. The water views are breathtaking!
After taking it all in, easily prepare and eat your own meal in our fully equipped kitchen and dining area (or outdoor gas grill), then relax further in the living room -- which has a flat-screen smart Netflix enabled television, cable, Wi-Fi wireless internet and DVD player -- or simply unplug and unwind to the natural symphony of the forest, as cooling breezes rustle the surrounding canopy outside. We even have a small library of beach reads for your enjoyment. Ahhh... blissful!
Christmas Winds as a whole is a well-maintained wood home with ceramic tile floors, native stonework and high ceilings. The atmosphere in the house is informal, and the home is ideal for one or two couples, or a relaxing honeymoon. The home is also good for a family with older children who can sleep on a separate level from parents. There is no maid service, but it is thoroughly prepared for guests and cleaned upon departure, and our house manager is happily on call for any questions. There are linens, beach and bath towels and a full laundry with washer and dryer, as well as beach chairs and some beach accessories and pool toys for guest use (snorkel fins and masks, boogie board, etc.).
Do feel free to email with any questions. We hope to see you soon on St. John!
Amenities at Private home with water views: Cruz Bay, beaches close by
Non-smoking
No pets allowed
Map of Cruz Bay
Ratings and reviews
8 / 10Excellent·Feb 2026
Host was excellent in communicating, as well as the local host Patti.Clean accommodation. Kiitchen well stocked.Great view from deck overlooking Chocolate Pond and Ocean! Outdoor gas grill was appreciated. Property has retro 60's feel. Secluded property, Iguanas in the treetops,saw a local deer on property!
8 / 10Excellent·Feb 2026
We had a nice 6-day visit. The house manager, Patti, was very welcoming and helpful throughout our stay. Location was very convenient to Cruz Bay with shopping, restaurants, and the Starfish Market for groceries. House had basic necessities and was clean; however, it could definitely use some remodeling/updates (especially in the bathrooms and kitchen). If you plan to cook, you’ll need to provide your own oils and spices. We appreciated the use of the washer/dryer and beach equipment.
10 / 10Outstanding·Jan 2026
Christmas Winds was perfect for our recent family vacation in St John. Of note, this rental is probably best suited for families with older children as the second bedroom is on the lower level and accessed from an entrance separate from the main living quarters. The location of the house is relatively private overlooking the water, but not far from Cruz Bay making it easy to enjoy many of the great restaurants and access to the National park and beautiful beaches. The house is well equipped with essentials, linens, beach towels and beach chairs and equipment. The owner and island host provided outstanding hospitality. There was good communication before our arrival and they promptly responded to questions we had during our stay. All this contributed to a wonderful vacation in St John!
6 / 10Average·Feb 2025
I value VRBO comments greatly in my choice of vacation properties, so I want to carefully convey some thoughts after a recent 9 day stay at Christmas Winds in St. John VI.Communications with Ashley Winchester, the owner's daughter were prompt and detailed. The onsite check-in and -out with Patti went perfectly.This is an older home,1940's age The kitchen is well supplied with implements, the stove is good and the microwave adequate. The Wifi, TVs, and ACs are good. Of note is that the 1st fl BR is framed out from the 1st fl interior. The walls do not reach the ceiling and the doors separating it from the LR are half clear glass. Thus, privacy might be compromised for some renters.Car parking is on the street level above the house. There are 18 steep steps down to the first floor entrance and 14 more steps down to the lower level entrance.A very difficult item for my wife and myself was the lack of light blocking window shades in both bedrooms. The very bright morning light made sleeping past 6:30 impossible, even with eye shades.Neither deck, both of which are excellent, had any sun umbrellas. For those of us that are conscious of the adverse effects of intense UV light on our skin, not having any shade made the use of the upper deck impossible to enjoy until late afternoon. Even the lower deck received strong direct sunlight for much of the day.St John is a wonderful vacation location! We hope you enjoy your visit as much as we did.
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Top rated by guests
9.5Outstanding
(50 Ratings)
"Christmas Winds was perfect for our recent family vacation in St John. Of note, this rental is probably best suited for families with older children as the second bedroom is on the lower level and ac..."
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