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.
In Season
Jan. 9, 2026 - April 15, 2026
$3745/wk for 2 people - 1 bedroom (main house only)
$4046/wk for 3 people - 2 bedroom
$4347/wk for 4 people - 2 bedroom
$4678/wk for 5 people - 3 bedroom
$4949/wk for 6 people - 3 bedroom
Off Season
April 16, 2026 - Dec. 15, 2026
$2310/wk for 2 people - 1 bedroom (main house only)
$2611/wk for 3 people - 2 bedroom
$2912/wk for 4 people - 2 bedroom
$3213/wk for 5 people - 3 bedroom
$3514/wk for 6 people - 3 bedroom
Holiday
Thanksgiving
Nov. 21 -29, 2026
$2611/wk for 2 people - 1 bedroom (main house only)
$2912/wk for 3 people - 2 bedroom
$3213/wk for 4 people - 2 bedroom
$3514/wk for 5 people - 3 bedroom
$3815/wk for 6 people - 3 bedroom
** Christmas/New Years
Dec. 16, 2026 - Jan. 8, 2027
$5964/wk for 2 - 6 people
** Christmas/New Year's: If arriving on Dec. 23rd, Dec. 24th or 25th a minimum number of nights may apply.
12.5% hotel tax/5% service charge
$59 non-refundable damage waiver
(covers up to the 1st $500 in accidental damage. Damage must be reported while on the island for it to be covered. Damage above $500 is the responsibility of the guest)