Villa in Cruz Bay
6 guests · 3 bedrooms · 3 baths
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About this villa rental
Tennis Cottage – Charming 3-Bedroom Villa with Private Pool in Chocolate Hole, St. John
Tennis Cottage is a charming 3-bedroom, 3-bath vacation home in Chocolate Hole on St. John, U.S. Virgin Islands, offering a private tropical setting, stunning south-facing views of Chocolate Hole Harbor and the Caribbean Sea, and a beautiful 40-foot private swimming pool.
Designed as two separate buildings—the main house and a private guest house—Tennis Cottage provides a wonderful combination of togetherness and privacy for families, couples, and small groups looking for a peaceful Caribbean vacation rental.
The main house features the air-conditioned great room, kitchen, dining area, and romantic king-bedroom master suite with private bath. A spacious covered deck extends the living space outdoors and provides a spectacular setting for relaxing, dining, and enjoying the tropical breezes. The separate guest house includes a private bedroom suite with its own bathroom, while the third bedroom is located on the lower level of the main house and opens directly toward the pool and expansive sun deck.
With Tesla solar panels and an automatic battery backup system, Tennis Cottage is designed for greater energy efficiency and added peace of mind during an island power interruption.
If you're searching for a private 3-bedroom St. John villa with a pool, ocean views, air conditioning, and a convenient location near Cruz Bay, Tennis Cottage is an inviting choice for your next tropical getaway.
Location – Chocolate Hole, St. John
Tennis Cottage is located in Chocolate Hole, one of St. John's established and peaceful residential neighborhoods, known for its luxury vacation villas and beautiful Caribbean views.
The home enjoys south-facing views overlooking Chocolate Hole Harbor and the Caribbean Sea. Despite being located near Tennis Villa, Tennis Cottage maintains its own privacy with a separate driveway and parking area. A scenic pathway connects the two properties, making it convenient for larger groups who rent both villas.
Location highlights include:
- Approximately 5–6 minutes by car to Cruz Bay
- Close to Cruz Bay restaurants, shops, grocery stores, and services
- Approximately 7–15 minutes to several beautiful Virgin Islands National Park beaches
- Peaceful Chocolate Hole neighborhood
- South-facing Caribbean Sea views
- Private parking and separate driveway
Tennis Cottage offers the best of both worlds: a quiet tropical retreat with beautiful water views, while remaining just a short drive from the restaurants, shopping, nightlife, and ferry terminal in Cruz Bay.
Living & Dining
The air-conditioned great room combines the living and dining areas into a comfortable gathering space filled with tropical breezes and beautiful views of Chocolate Hole. Guests can relax indoors or move seamlessly onto the spacious covered deck to enjoy the Caribbean surroundings.
Amenities include:
- Air-conditioning
- Wireless internet
- 32-inch flat-screen cable TV/DVD
- Bluetooth speaker
- Indoor dining for 6
- Outdoor dining on the covered deck
- Washer/dryer on the lower level
The covered upper-level deck is one of the home's favorite gathering spaces, offering a peaceful place to enjoy morning coffee, an al fresco meal, or an evening under the stars overlooking the harbor.
Kitchen
The fully equipped kitchen makes it easy to prepare everything from a quick breakfast to a full dinner.
Kitchen and outdoor cooking amenities include:
- Fully equipped kitchen
- Gas stove/oven
- Refrigerator
- Dishwasher
- Microwave
- Coffeemaker
- Toaster
- Cooking and serving essentials
- Gas BBQ grill in the courtyard
The adjacent dining spaces make it easy to enjoy meals indoors or outside while taking in the tropical scenery.
Three Private Bedrooms
Each of Tennis Cottage's three bedrooms is designed with comfort and privacy in mind. All bedrooms feature air conditioning, ceiling fans, 32-inch cable flat-screen TVs and private tiled bathrooms. Guests can also take advantage of the refreshing natural Caribbean breezes.
Primary Bedroom – Main House
The romantic primary suite is located off the main house great room and features a king-size bed, with access to a bathroom just outside the bedroom door. Its comfortable setting and proximity to the main living area make it an ideal retreat.
Guest House Suite – King or Two Twins
The private guest house features a second inviting bedroom suite with a king-size bed that can be configured as two twin beds. The suite has its own private tiled bathroom with an outdoor garden shower and opens directly onto the courtyard, creating a quiet and secluded space for guests.
Lower-Level Bedroom – Queen
The third bedroom is located on the lower level of the main house and features a queen-size bed, cozy sitting area, private tiled bathroom, and beautiful views overlooking the pool and Chocolate Hole. Its direct access to the pool and sun deck makes this bedroom particularly appealing for guests who enjoy easy access to the outdoor living areas.
Private Pool & Outdoor Living
The centerpiece of Tennis Cottage's outdoor space is the expansive 40-foot private swimming pool, surrounded by a spacious sun-drenched deck.
Outdoor amenities include:
- 40-foot private swimming pool
- Spacious pool deck
- Covered upper-level deck
- Outdoor dining
- Gas BBQ grill
- Tropical landscaping
- Spectacular Chocolate Hole Harbor views
- South-facing Caribbean Sea views
Spend the day lounging beside the pool, enjoy an outdoor meal overlooking the harbor, or settle onto the covered deck as the Caribbean sky changes color in the evening.
Solar Power & Backup Battery
Tennis Cottage features Tesla solar panels and an automatic battery backup system. The solar-powered system provides an energy-conscious way to enjoy your Caribbean vacation and offers additional peace of mind should the island experience a temporary power interruption.
Rent Tennis Cottage & Tennis Villa Together
For larger families and groups, Tennis Cottage can be rented together with Tennis Villa, creating an impressive 7-bedroom St. John vacation estate.
Rent the properties separately for a more intimate getaway, or combine them for a larger gathering where guests can enjoy multiple bedrooms, living spaces, and private outdoor areas while remaining close to one another.
Tennis Cottage combines the charm and intimacy of a Caribbean cottage with the amenities, privacy, pool, and spectacular views guests seek in a St. John vacation rental.
Frequently Asked Questions (FAQ):
Is there on-island assistance if we need help during our stay?
Yes! We have local staff on the island. Our friendly team is available to answer questions, provide recommendations, and assist with anything you may need during your stay, helping ensure a smooth and enjoyable vacation.
What grocery stores are closest to Tennis Cottage?
- St. John Market
- Starfish Market
- Dolphin Market
- Pine Peace Market
Do I need a jeep rental when staying at Tennis Cottage and is parking available?
Yes. A jeep rental is recommended when visiting St. John so you can easily explore the island’s beautiful beaches, national park, restaurants, and shops. Cruz Bay is only a short 5-minute drive from the home. The home includes parking.
What are the gas stations on St John?
- E.C. Gas
- Race Track Gas Station
- Midway Gas Station
There aren't any gas stations in Coral Bay
Is any beach gear included with the rental?
Yes, beach towels, beach chairs, and a cooler are included.
What are the nicest beaches on St. John?
The nicest beaches are located in the National Park, along the North side of the island. These beaches are a 10–20 minute drive by jeep from Cruz Bay, including:
Hawksnest, Trunk Bay, Maho, Francis Bay, to name a few. Explore the island to find your favorite.
What are some of the restaurants in Cruz Bay?
There are amazing restaurants from casual to fine dining. Here are some of our recommendations: St John Back Bar, 1864, Hightide, Morgan's Mango, Ocean 362, and Cafe Roma, to name a few.
What are some activities available on St John?
- If you have never been to St John - take an island tour.
- Go to a different beach each day to find your favorite
- Drive over to Coral Bay to explore the quieter side of the island - have lunch at Skinny Leg's
- Go on a boat excursion
- Hiking - Reef Bay Trail and Ram's Head -
- Snorkeling, Scuba Diving, Paddle boards, Kayaking
- Do nothing at all - just let the restorative ambiance of St John replenish you
What provisioning companies, private chef services, and boating excursions are recommended?
- Provisioning: Landlubber Logistics, Dolphin Market, and Starfish Market
- Chefs: St. John Catering & DSC Dining
- Boat Excursions: Flyaway Charters, Sunshine Day Dream Charters. Scheduled excursions: Stormy Pirates
Tennis Cottage is a charming 3-bedroom, 3-bath vacation home in Chocolate Hole on St. John, U.S. Virgin Islands, offering a private tropical setting, stunning south-facing views of Chocolate Hole Harbor and the Caribbean Sea, and a beautiful 40-foot private swimming pool.
Designed as two separate buildings—the main house and a private guest house—Tennis Cottage provides a wonderful combination of togetherness and privacy for families, couples, and small groups looking for a peaceful Caribbean vacation rental.
The main house features the air-conditioned great room, kitchen, dining area, and romantic king-bedroom master suite with private bath. A spacious covered deck extends the living space outdoors and provides a spectacular setting for relaxing, dining, and enjoying the tropical breezes. The separate guest house includes a private bedroom suite with its own bathroom, while the third bedroom is located on the lower level of the main house and opens directly toward the pool and expansive sun deck.
With Tesla solar panels and an automatic battery backup system, Tennis Cottage is designed for greater energy efficiency and added peace of mind during an island power interruption.
If you're searching for a private 3-bedroom St. John villa with a pool, ocean views, air conditioning, and a convenient location near Cruz Bay, Tennis Cottage is an inviting choice for your next tropical getaway.
Location – Chocolate Hole, St. John
Tennis Cottage is located in Chocolate Hole, one of St. John's established and peaceful residential neighborhoods, known for its luxury vacation villas and beautiful Caribbean views.
The home enjoys south-facing views overlooking Chocolate Hole Harbor and the Caribbean Sea. Despite being located near Tennis Villa, Tennis Cottage maintains its own privacy with a separate driveway and parking area. A scenic pathway connects the two properties, making it convenient for larger groups who rent both villas.
Location highlights include:
- Approximately 5–6 minutes by car to Cruz Bay
- Close to Cruz Bay restaurants, shops, grocery stores, and services
- Approximately 7–15 minutes to several beautiful Virgin Islands National Park beaches
- Peaceful Chocolate Hole neighborhood
- South-facing Caribbean Sea views
- Private parking and separate driveway
Tennis Cottage offers the best of both worlds: a quiet tropical retreat with beautiful water views, while remaining just a short drive from the restaurants, shopping, nightlife, and ferry terminal in Cruz Bay.
Living & Dining
The air-conditioned great room combines the living and dining areas into a comfortable gathering space filled with tropical breezes and beautiful views of Chocolate Hole. Guests can relax indoors or move seamlessly onto the spacious covered deck to enjoy the Caribbean surroundings.
Amenities include:
- Air-conditioning
- Wireless internet
- 32-inch flat-screen cable TV/DVD
- Bluetooth speaker
- Indoor dining for 6
- Outdoor dining on the covered deck
- Washer/dryer on the lower level
The covered upper-level deck is one of the home's favorite gathering spaces, offering a peaceful place to enjoy morning coffee, an al fresco meal, or an evening under the stars overlooking the harbor.
Kitchen
The fully equipped kitchen makes it easy to prepare everything from a quick breakfast to a full dinner.
Kitchen and outdoor cooking amenities include:
- Fully equipped kitchen
- Gas stove/oven
- Refrigerator
- Dishwasher
- Microwave
- Coffeemaker
- Toaster
- Cooking and serving essentials
- Gas BBQ grill in the courtyard
The adjacent dining spaces make it easy to enjoy meals indoors or outside while taking in the tropical scenery.
Three Private Bedrooms
Each of Tennis Cottage's three bedrooms is designed with comfort and privacy in mind. All bedrooms feature air conditioning, ceiling fans, 32-inch cable flat-screen TVs and private tiled bathrooms. Guests can also take advantage of the refreshing natural Caribbean breezes.
Primary Bedroom – Main House
The romantic primary suite is located off the main house great room and features a king-size bed, with access to a bathroom just outside the bedroom door. Its comfortable setting and proximity to the main living area make it an ideal retreat.
Guest House Suite – King or Two Twins
The private guest house features a second inviting bedroom suite with a king-size bed that can be configured as two twin beds. The suite has its own private tiled bathroom with an outdoor garden shower and opens directly onto the courtyard, creating a quiet and secluded space for guests.
Lower-Level Bedroom – Queen
The third bedroom is located on the lower level of the main house and features a queen-size bed, cozy sitting area, private tiled bathroom, and beautiful views overlooking the pool and Chocolate Hole. Its direct access to the pool and sun deck makes this bedroom particularly appealing for guests who enjoy easy access to the outdoor living areas.
Private Pool & Outdoor Living
The centerpiece of Tennis Cottage's outdoor space is the expansive 40-foot private swimming pool, surrounded by a spacious sun-drenched deck.
Outdoor amenities include:
- 40-foot private swimming pool
- Spacious pool deck
- Covered upper-level deck
- Outdoor dining
- Gas BBQ grill
- Tropical landscaping
- Spectacular Chocolate Hole Harbor views
- South-facing Caribbean Sea views
Spend the day lounging beside the pool, enjoy an outdoor meal overlooking the harbor, or settle onto the covered deck as the Caribbean sky changes color in the evening.
Solar Power & Backup Battery
Tennis Cottage features Tesla solar panels and an automatic battery backup system. The solar-powered system provides an energy-conscious way to enjoy your Caribbean vacation and offers additional peace of mind should the island experience a temporary power interruption.
Rent Tennis Cottage & Tennis Villa Together
For larger families and groups, Tennis Cottage can be rented together with Tennis Villa, creating an impressive 7-bedroom St. John vacation estate.
Rent the properties separately for a more intimate getaway, or combine them for a larger gathering where guests can enjoy multiple bedrooms, living spaces, and private outdoor areas while remaining close to one another.
Tennis Cottage combines the charm and intimacy of a Caribbean cottage with the amenities, privacy, pool, and spectacular views guests seek in a St. John vacation rental.
Frequently Asked Questions (FAQ):
Is there on-island assistance if we need help during our stay?
Yes! We have local staff on the island. Our friendly team is available to answer questions, provide recommendations, and assist with anything you may need during your stay, helping ensure a smooth and enjoyable vacation.
What grocery stores are closest to Tennis Cottage?
- St. John Market
- Starfish Market
- Dolphin Market
- Pine Peace Market
Do I need a jeep rental when staying at Tennis Cottage and is parking available?
Yes. A jeep rental is recommended when visiting St. John so you can easily explore the island’s beautiful beaches, national park, restaurants, and shops. Cruz Bay is only a short 5-minute drive from the home. The home includes parking.
What are the gas stations on St John?
- E.C. Gas
- Race Track Gas Station
- Midway Gas Station
There aren't any gas stations in Coral Bay
Is any beach gear included with the rental?
Yes, beach towels, beach chairs, and a cooler are included.
What are the nicest beaches on St. John?
The nicest beaches are located in the National Park, along the North side of the island. These beaches are a 10–20 minute drive by jeep from Cruz Bay, including:
Hawksnest, Trunk Bay, Maho, Francis Bay, to name a few. Explore the island to find your favorite.
What are some of the restaurants in Cruz Bay?
There are amazing restaurants from casual to fine dining. Here are some of our recommendations: St John Back Bar, 1864, Hightide, Morgan's Mango, Ocean 362, and Cafe Roma, to name a few.
What are some activities available on St John?
- If you have never been to St John - take an island tour.
- Go to a different beach each day to find your favorite
- Drive over to Coral Bay to explore the quieter side of the island - have lunch at Skinny Leg's
- Go on a boat excursion
- Hiking - Reef Bay Trail and Ram's Head -
- Snorkeling, Scuba Diving, Paddle boards, Kayaking
- Do nothing at all - just let the restorative ambiance of St John replenish you
What provisioning companies, private chef services, and boating excursions are recommended?
- Provisioning: Landlubber Logistics, Dolphin Market, and Starfish Market
- Chefs: St. John Catering & DSC Dining
- Boat Excursions: Flyaway Charters, Sunshine Day Dream Charters. Scheduled excursions: Stormy Pirates
Amenities
Non-smoking
No pets allowed
Map of Cruz Bay
Ratings and reviews
Summary of reviewsThe property provided everything we needed. The separate bedrooms were comfortable and private. The management took very good care of us. We will definitely be back.
10 / 10Outstanding·Feb 2022
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.
10 / 10Outstanding·Apr 2021
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.
10 / 10Outstanding·Feb 2021
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.
10 / 10Outstanding·Oct 2016
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.
$$$$
Top rated by guests
10Outstanding
(5 Ratings)
The property provided everything we needed. The separate bedrooms were comfortable and private. The management took very good care of us. We will definitely be back.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
