Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views
Description: Discover the enchanting Tennis Cottage, a delightful 3-bedroom, 3-bath home boasting a stunning pool. With its private and tropical atmosphere, Tennis Cottage is the perfect retreat, featuring two separate buildings: the main house and a cozy guest house. The main house offers a seamless living space, including the kitchen and dining areas, alongside a romantic master bedroom with an ensuite bath.
A spacious covered deck provides a fantastic vantage point to unwind and soak in the breathtaking views of Chocolate Hole while enjoying the captivating Caribbean nights.
The guest house hosts a second private and inviting bedroom with its own bath, while the third bedroom, located on the lower level of the main house, opens directly to the expansive 40-foot pool and sun-drenched sundeck.
Equipped with Tesla solar panels, the main house ensures an eco-friendly stay and should there ever be a power interruption on the island, the automatic battery backup system has you covered.
If you are looking for a charming Caribbean cottage, look no further; Tennis Cottage awaits your arrival. Make your reservations now and plan your tropical getaway.
Location: Positioned in a serene enclave, Tennis Cottage provides stunning south-facing vistas of Chocolate Hole Harbor and the shimmering Caribbean Sea. Despite its proximity to Tennis Villa, both residences offer complete privacy, with separate driveways and parking areas. A scenic path links the two villas, making it easy to transition between spaces. Chocolate Hole is a well-established, tranquil neighborhood characterized by luxury residential villas.
In just a 5-6 minute drive, you can reach the bustling shops, restaurants, and grocery stores of Cruz Bay, while the island's beautiful National Park beaches are only a short 7 to 15-minute drive away.
Living and Dining: Inside, the air-conditioned living and dining area exudes relaxation, enhanced by captivating views and refreshing breezes. Stay connected with wireless internet and enjoy entertainment through the 32-inch flat-screen cable TV/DVD and Bluetooth speaker. Dine al fresco on the upper-level deck, or inside at another table for six. A convenient washer/dryer can be found on the lower level for added ease.
Kitchen: The fully equipped kitchen caters to all culinary needs, whether you're preparing snacks or crafting gourmet meals, complete with a gas BBQ grill in the courtyard.
Bedrooms: Each of the three bedrooms is designed for comfort, featuring 32" cable flat-screen TVs, Blu-ray DVD players, air conditioning, and ceiling fans, or opt for the refreshing natural breezes. The main house master suite features a luxurious king bed and is conveniently located off the great room. The guest house's private master suite also boasts a king bed (or two twin beds) and opens directly to the courtyard. The third bedroom, on the lower level, offers a queen bed, a cozy sitting area, and stunning views of the pool and Chocolate Hole. All bedrooms are paired with well-appointed tiled baths for added convenience.
Tennis Villa can be rented simultaneously with Tennis Cottage, creating a remarkable 7-bedroom estate, or each villa can stand alone for a more intimate experience.
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Amenities
Pool
Kitchen
Washing machine
Free WiFi
Air conditioning
Sea view
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Virgin Islands National Park - 4 min drive - 3.0 km
Getting around
St. Thomas (SPB-St. Thomas Seaplane Base) - 63 min drive
Restaurants
Woody's Seafood Saloon - 6 min drive
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Frequently asked questions
Does Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views have a pool?
Yes, this property has a pool.
How much does it cost to stay at Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views?
As of 3 Apr, 2026, prices found for a 1-night stay for 2 adults at Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views on 1 Jul, 2026 start from S$644, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views pet-friendly?
No, pets are not allowed at this property.
What time is check-in at Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views?
Check-in begins at 4:00 PM.
What time is check-out at Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views?
Checkout is at 10:00 AM.
Where is Chill by the Pool, Enjoy the Views: Tennis Cottage with A/C and Chocolate Hole Views located?
Situated near the beach, this villa is 0.4 mi (0.6 km) from Great Cruz Bay and 1.6 mi (2.6 km) from Virgin Islands National Park. Chocolate Hole Beach and Rendezvous Bay are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
we loved this villa's location and it had everything we needed. Three bedrooms are all separate and private and comfortable. Management company took very good care of us and we will be back to tennis cottage next year.
Response from VrboOwner on 18 Mar, 2020
Thank you for your review! We are happy to hear you enjoyed your stay at Tennis Cottage! We look forward to having you stay with us again!
Archival
10/10 Excellent
6 Oct, 2016
RELAXING
Cozy cottage just outside of town. Perfect spot for us. We booked our next trip for next year and look forward to staying at tennis cottage again.
Response from VrboOwner on 18 Mar, 2020
Thank you for your review! We are pleased you have already reserved for next year and look forward to having you stay with us again!
If you’re looking for a quiet spot on St John, Tennis Cottage is a great option. The cottage is appropriately named as it’s more cottage than villa, but we really liked the charm of the place. There are 3 bdrms, one in the basement walks out to the pool. Upstairs is a nice open air porch that overlooks Chocolate Hole. The property is situated lower on the ridge line between Chocolate Hole and little Cruz Bay which doesn’t afford big sweeping views, but there is a very nice view of the Hole and beyond out to open water. The main house consists of a kitchen, living room and dining area in an open floor plan. There is also a bedroom with a large closet. In addition, there is a separate building with a bedroom. All three bedrooms have a bathroom. Because of the layout, this cottage probably isn’t ideal for a family with young children who you don’t want sleeping separately from the adults. But if you want a place with some privacy among the bdrms, this set up is perfect. Many people walk and run along the road just in front of the cottage so it’s a good place to get a little exercise in the mornings or early evenings. It is possible to walk down a short but steep landing to gain access to the beach at little Cruz Bay and the Westin. We walked down to let the kids swim and we had dinner at the beach restaurant at the Westin. That walkability factor is a big plus for this location as the property also feels isolated and quiet. Lastly, the management company and all of the good people there are really enjoyable and made our stay wonderful.
Troy H.
Stayed 7 nights in Mar 2021
Response from VrboOwner on 18 Apr, 2021
Thank you Troy. We are happy you enjoyed your stay. Thank you. Diane, Caribbean villas
We had a wonderful time. The house provided everything we could want or need. Our welcome surprise in the fridge was perfect & came in handy. My parents were in the main level & my husband and I chose the pool level room, it was great having the separate areas. We will definitely be back.
Stocked with everything you would possible need for a beach vacation. The property manager was constantly in communication with you and easy to reach. The full kitchen had anything you would need to prepare a meal. It was easily found and accessible to taxi services so getting a car wasn’t exactly necessary. It is very close to the main house so you can hear people outside and vice versa, overall a very nice stay I would book again.
Sarah B.
Stayed 7 nights in Feb 2021
About the host
Hosted by Caribbean Villas of St. John
Languages:
English
Premier Host
They consistently provide great experiences for their guests