Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon
House in Virgin Islands (U.S.)
10 guests · 5 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
About this house rental
Named because of it's magnificent views, Triton's Overlook is situated right on the water's edge and offers stunning,unobstructed views of the Caribbean Sea, nine islands including the British Virgin Islands, and St John. Triton's Overlook, a former local estate known as Villa Maitland, has undergone an extensive renovation over the past few years. While much of the house is new, nods to the past still abound-from the massive mahogany doors , to the old West Indies parquet floor in the Master Bedroom. And with large glass windows and doors spanning across the open-concept home, you can take in the unbelievable views and enjoy the gentle breeze from the couch, or even while working in the kitchen. From the comfort of the Overlook Family Room and porch look for large yachts passing thru Pillsbury Sound on their way to St John or look below thru the clear Caribbean water for sea rays, dolphins and fish swimming by . There is always something to look for. Our photos barely do it justice!
The fully optioned gourmet kitchen includes a dishwasher, five burner gas stove with dual-oven, microwave, toaster, and Keurig. Plenty of space for all the "cooks" in the group !
The Theater Room, just off of the main living area, offers a 75” high definition SmartTV with surround sound in a enclosed setting for twelve to enjoy a special show or movie.
All five bedrooms feature en-suite bathrooms and King size beds. Four bedrooms have "down island views". The Master Bedroom and two others are located off of the main living area. The master bedroom is palatial, offering a full view of the Caribbean from the comfort of a king size Sleep Number bed. It also includes a large walk-in-closet with a bathroom featuring an open floor shower big enough for two (gotta save water). A second bedroom also offers a Sleep Number king size bed, an ocean view and opens up to a private balcony. A third bedroom offers a king size bed high open ceiling and a view of the water overlooking gorgeous grounds.This room is convenient to the main living area and makes a perfect Au Pair suite. Two bedrooms on the lower level offer the same ocean view as above, and open up to a private ground level porch for easy access to the pool and grounds. ( Great for those late night swims ).
The downstairs entertainment area includes a wet bar, ice maker, large curved high definition Smart TV and a large bar top for games, eating, drinking or just gathering to talk or meet to plan the day's activities. The sliding glass doors open directly to the pool deck.
The house is fully air conditioned and has a large generator to power the entire house in case of power outages during your stay. Internet is available through the house and pool area for those who need to stay connected. For those music lovers Sonos services the pool deck, lower level activity room, theater room, foyer/dining room and master bedroom. All TV’s are Smart TV’s with Net Flix, Amazon Prime and Utube.
NEED MORE BEDROOMS ? GUEST HOUSE CAN ADD UP TO TWO MORE BEDROOMS:
The property also features a separate two bedroom guest house , Triton’s Hideaway, which is only rented with the house. The spacious master bedroom features a king size bed with large en-suite bathroom. The second bedroom is a loft bedroom with a king size bed and private bathroom. Downstairs, which is on level with the pool deck and grounds, features a family room, a full bathroom, and kitchen all with direct water view. The guest house is fully air conditioned, has its own generator, Wi-Fi and Smart TV’s. When renting the main house you can rent the Guest House’s Master Bedroom alone as an additional separate bedroom or the full house. Your choice. The guest house is not included in the price for the house so please ask for a quote adding the Guest house. The Guest House is only available as additional accommodations when renting the full property. We never rent the guest house out to a different party. The entire property is only available to you. ADDING TRITON’S HIDEAWAY, ( the guest house ) to TRITON’S OVERLOOK CAN INCREASE THE NUMBER OF GUESTS FROM 10 TO 12, OR 14.
Triton's Overlook is conveniently located about one mile outside of Red Hook on the East End of St. Thomas. Red Hook offers many restaurants and bars, shopping, groceries, a marina, and the ferry to St. John and the British Virgin Islands. Many tours and charters are also booked out of Red Hook. What makes Triton's Overlook so special and unique is that there are so many areas to escape to your "own space", whether inside the house or outside on the expansive, lush grounds. It's more than just a house, it's a experience that very few can match. With over one acre of enclosed grounds, fruit and palm trees, and other tropical flowering plants there is always something new to see every day. Enjoy the breeze under the palm trees and sea grapes on your own private beach area, step directly and swim in you own lagoon, snorkel on the coral reef right in front of the house, or lay out at the pool. Once you've arrived at Triton's Overlook, the rest is up to you !
In addition to Triton’s Overlook we have owned the adjacent property, Caribbean Castaway since 2006. If you find Triton’s Overlook booked for the dates you requested or are interested in booking the two properties together, (for a total of 13 bedrooms) accommodating up to 26 guests in beds with their own bathroom. check out Caribbean Castaway, property #320776.
The fully optioned gourmet kitchen includes a dishwasher, five burner gas stove with dual-oven, microwave, toaster, and Keurig. Plenty of space for all the "cooks" in the group !
The Theater Room, just off of the main living area, offers a 75” high definition SmartTV with surround sound in a enclosed setting for twelve to enjoy a special show or movie.
All five bedrooms feature en-suite bathrooms and King size beds. Four bedrooms have "down island views". The Master Bedroom and two others are located off of the main living area. The master bedroom is palatial, offering a full view of the Caribbean from the comfort of a king size Sleep Number bed. It also includes a large walk-in-closet with a bathroom featuring an open floor shower big enough for two (gotta save water). A second bedroom also offers a Sleep Number king size bed, an ocean view and opens up to a private balcony. A third bedroom offers a king size bed high open ceiling and a view of the water overlooking gorgeous grounds.This room is convenient to the main living area and makes a perfect Au Pair suite. Two bedrooms on the lower level offer the same ocean view as above, and open up to a private ground level porch for easy access to the pool and grounds. ( Great for those late night swims ).
The downstairs entertainment area includes a wet bar, ice maker, large curved high definition Smart TV and a large bar top for games, eating, drinking or just gathering to talk or meet to plan the day's activities. The sliding glass doors open directly to the pool deck.
The house is fully air conditioned and has a large generator to power the entire house in case of power outages during your stay. Internet is available through the house and pool area for those who need to stay connected. For those music lovers Sonos services the pool deck, lower level activity room, theater room, foyer/dining room and master bedroom. All TV’s are Smart TV’s with Net Flix, Amazon Prime and Utube.
NEED MORE BEDROOMS ? GUEST HOUSE CAN ADD UP TO TWO MORE BEDROOMS:
The property also features a separate two bedroom guest house , Triton’s Hideaway, which is only rented with the house. The spacious master bedroom features a king size bed with large en-suite bathroom. The second bedroom is a loft bedroom with a king size bed and private bathroom. Downstairs, which is on level with the pool deck and grounds, features a family room, a full bathroom, and kitchen all with direct water view. The guest house is fully air conditioned, has its own generator, Wi-Fi and Smart TV’s. When renting the main house you can rent the Guest House’s Master Bedroom alone as an additional separate bedroom or the full house. Your choice. The guest house is not included in the price for the house so please ask for a quote adding the Guest house. The Guest House is only available as additional accommodations when renting the full property. We never rent the guest house out to a different party. The entire property is only available to you. ADDING TRITON’S HIDEAWAY, ( the guest house ) to TRITON’S OVERLOOK CAN INCREASE THE NUMBER OF GUESTS FROM 10 TO 12, OR 14.
Triton's Overlook is conveniently located about one mile outside of Red Hook on the East End of St. Thomas. Red Hook offers many restaurants and bars, shopping, groceries, a marina, and the ferry to St. John and the British Virgin Islands. Many tours and charters are also booked out of Red Hook. What makes Triton's Overlook so special and unique is that there are so many areas to escape to your "own space", whether inside the house or outside on the expansive, lush grounds. It's more than just a house, it's a experience that very few can match. With over one acre of enclosed grounds, fruit and palm trees, and other tropical flowering plants there is always something new to see every day. Enjoy the breeze under the palm trees and sea grapes on your own private beach area, step directly and swim in you own lagoon, snorkel on the coral reef right in front of the house, or lay out at the pool. Once you've arrived at Triton's Overlook, the rest is up to you !
In addition to Triton’s Overlook we have owned the adjacent property, Caribbean Castaway since 2006. If you find Triton’s Overlook booked for the dates you requested or are interested in booking the two properties together, (for a total of 13 bedrooms) accommodating up to 26 guests in beds with their own bathroom. check out Caribbean Castaway, property #320776.
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Map of Virgin Islands (U.S.)
££££
Reviews
10.0
Breathtakingly beautiful Villa with great Amenities. HOUSE IS HUGE! plenty of room for 8. Loved it!
10.0
Best Vacation EVER. There were 10 of us in the main house (8 adults and 2 teenagers) and 1 adult in the guest house master bedroom. There was ample space for us to all sprawl out and do our own thing during the day and regroup in the evenings. The views are simply breathtaking. We had incredible weather all week and took full advantage of the pool, private beach and snorkeling cove. Red Hook offered everything we needed off-property (market, restaurants Etc.) which was convenient. The property managers were very friendly and helpful. We were all sad to see the week come to an end and agreed that this vacation will be hard to beat. Thank you for sharing your piece of paradise with us!
10.0
Spent an amazing week in this beautiful property celebrating my 50th birthday with 10 of my best friends. House was amazing with plenty of space for everyone.
10.0
Beautiful villa room for all! Location to other beaches & excursions was easy. Pool was a big hit.. especially after beach days..lots of nighttime swimming.. would definitely recommend to friends & family..
10.0
We had a wonderful week at Triton’s Overlook. It’s a beautiful, clean, spacious house with so many extras. The large kitchen was perfect for our group of 10 and has everything you would need. We spent lots of time in the pool and on the deck. Several of the kids snorkeled right off the property. The rooms were all clean and spacious, and they all had lovely views of the Caribbean. The theater room was perfect for a family movie night.
We were able to take a short walk over to Sapphire Beach for a change of pace. We spent two days exploring the waters around the islands. We snorkeled, hiked, and spent time at Scott beach which has some of the clearest waters I’ve ever seen. The kids did a cliff jump on the other side of Thatch Cay which is the island you can see just north of the house.
There were rolling power outages for a few days, but it didn’t affect us since the home has a generator. The property managers were very helpful with any questions we had.
If you get the chance, stay here- you won’t regret it!
10.0
All was as described and was perfect for our group of 9. Beautiful views and a wonderful property that was clean, had tons of space, and everything you need for a home away from home. Thank you!
10.0
killer house and location and great for a large family with kids or a couple of families with kids
10.0
The pictures do not do this property justice. It is so beautiful inside and out. All the high end finishes and decorating was very pleasing to the eye. Beds were comfortable and we had everything we needed. A few of the remote blinds didn’t work which obstructed our view a bit from the kitchen but we did not let that get in our way of having a fabulous time. Thank you for sharing your piece of paradise with us!
The Weidner Family
10.0
Loved the house, beach and lagoon. The view was amazing. Enjoyed visiting several beaches on the Virgin Islands.
10.0
Gorgeous home and views of all the islands. Our group of 9 had an amazing stay at Tritons Overlook. Plenty of space for gathering together or looking for a little alone time. Close to Sapphire Beach (beautiful beach and restaurants) and Marina ( Sunshine Charters will pick you up there for excursions) as well as over the hill from Red Hook( great restaurants). House manager was there when needed and we needed for nothing. Don’t delay and book your stay.
10.0
Our family of 8 (all adults) stayed for 1 week. House is exactly as described. Beautiful location, great snorkeling, pool & beach area were perfect for hanging out and relaxing. It was a wonderful setting for a family vacation. HIGHLY RECOMMEND!!!!!
10.0
We stayed at this property 10 years ago when it was Villa Maitland. It was spectacular then and is even more beautiful now with all the wonderful updates.
My family was so excited to be able to repeat this trip. This was a gift to my adult children this year.
This house is perfect for an all adult family. Plenty of room to spread out. We also included a few friends who rented the guest house.
I would highly recommend this home. The owner was very responsive during the rental process and the property managers were extremely responsive and knowledgeable about the property.
This home and location should be on everyone’s bucket list.
Thank you for sharing your home with my family.
10.0
The home is beautiful and the snorkeling at the house is fantastic.
10.0
House was roomy enough for our group to stay. Beautiful living rooms on the main floor and having multiple fridges, multiple trash cans, and ice-maker was a huge plus. Hosts and property management were easy to communicate with and helpful throughout our stay. Biggest bonus was the little beach and amazing snorkeling in the backyard
10.0
Place was amazing. Enjoyed the stay and the property managers were on top of everything.
10.0
A beautiful house and property. Best location we have rented for vacation. Pictures and descriptions on the VRBO website does not do it justice. Management meet our expectations with flying colors. We are planning next years trip for 2 weeks
10.0
Thank you for everything!
10.0
This is a fantastic property and UNBEATABLE LOCATION! We were a party of 7, including 3 teenagers and our 8 yo twin boys. Honestly, the house was probably overboard for a family of our size, but my teenagers won’t complain about having their own rooms and king size beds! It’s an older home, but remodeling over the years has kept it from feeling dated. The common areas are enormous and beautifully furnished. The views from the living room and all the bedrooms are stunning. The kitchen is well stocked and there’s lots of items left from previous guests; we utilized the coffee and some of the booz, but preferred to pick up what we needed from Moe’s in Redhook when we got there. The theatre room was a great place for the twins to watch TV, either early in the mornings or before bed after a long day in the sun. The pool and lagoon are as awesome as all the previous reviews indicate, however, we didn’t utilize them as much as most might because we were out and about every day. We snorkeled from the lagoon once, but it was pretty windy and the waters were a little rough compared to all the other beaches (8) we went. My wife and I had coffee and fruit at the pool every morning which was delightful, and the twins had a hay day finding and observing all the iguanas around the house! Dave and Dawn were great… responsive to the few things we had to ask about, and they left us a bottle of rum, juices and a fruit basket to kick off our stay! Thank you for the hospitality!
10.0
This house is amazing!! Plenty of room for everyone and very convenient location to Redhook for restaurants, shopping and bars!! Had a wonderful time and can’t wait to visit again!! Dawn and Dave were wonderful for any questions we had!!
10.0
We had a great time and the house was big, beautiful and perfect for us. We each had our own space but could come together for food, cards or just hanging by the pool and beach.
10.0
Our family of eight stayed at this property over Christmas and New Years. The Smith Bay Estate is near Sapphire Beach and Red Hook and so it is convenient to most everything you need on St. Thomas.
The check-in process was great. Stores were closing early on Christmas eve and thanks to the owner, we were able to utilize the garage fridge to store items while we went to the airport to gather family members.
The property itself is gorgeous. It sits right on the water and the unit was well-equipped with items in the pantry (foods and spices) and there were plenty of plates, utensils, and cookware to meet your culinary needs. There were two large refrigerators, two trash receptacles, two washers and two dryers, and even an ice maker.
The living, dining, and bedroom areas were spacious and comfortable. Towels were big and plentiful and it was easy to fall into vacation mode while staying here.
Some of the best snorkeling on the island is right out front of the property. The current was sometimes strong so do take precautions before venturing out. There were many hard and soft corals, lots of fish, and we even spotted nudibranch (sea slugs) on the fan coral.
If you are considering a destination with a large family, Smith Bay Estate is a solid contender.
10.0
We were 2 families with all adult children. This house was perfect for us. The owner and property were amazing and very responsive.
10.0
This is a fantastic property. I don't think I could have picked a better one. We did some touring of the islands and beaches but very much enjoyed just hanging out at the pool and private beach. The kitchen was very well equipped and we ate out only once at Pangea which is right next door.
10.0
This is a beautiful property with amazing access to world class snorkeling right in the back yard. Several media spaces kept our multiple families from being on top of one another for the week. One of our favorite things was sitting on the balcony overlooking the ocean while enjoying a cup of coffee each morning.
10.0
The property is fabulous and exactly what we needed. We rented the entire villa including the guest house. The property had everything we needed and wanted. We had our own little beach with great snorkeling off the the rocks. The location is a 5min drive to Red Hook area for nightlife. Dawn and Dave are 5 star property mangers. Very responsive and helpful in planning our excursions. Our group did a lot of early morning meditation, mindfulness, and yoga in the grass area near the pool- please be ware, the misters come on around 6/7am....we found out the hard way 🤣 . Overall the property is well maintained and is taken care of with love. My biggest problem, was remembering where in this huge place did I sit my drink🤗
10.0
A perfect gem
Great house and perfect for family vacation… highly recommended
10.0
Stunning
The pictures don’t due this place justice! It is breathtaking. When you first walk in the front door all you see is gorgeous ocean right from those huge glass doors right off the main level. The place is huge. Lots of marble floors. If you have elderly or very young note that there are a few stairs to get into the house from the driveway and steps to get into the master bedroom. These were an unexpected hurdle for my mother in a wheelchair but once she was in the house she didn’t want to leave that amazing view and all was well. The large marble stairs were a little nervous for me with our little one with wet feet but there were no issues, we were careful. The reef at the private cove opening to the ocean is full of beautiful purple fan corals and lots of fish, even large schools of blue tangs. It was amazing!
10.0
50th Celebration
We celebrated our 50th wedding anniversary and our Granddaughter’s 20th birthday. We loved Triton Overlook. The views are amazing from every room. Loved the pool right on the water and having our own private beach. There were 12 of us and the house never felt crowded at all. Plenty of room wherever we gathered. We chartered a yacht from Elixir charter. David, Janet and Angie were wonderful! We also charted a 47 foot Sea Ray from Ocean Runner. Chris and Jenny were also wonderful. Doug and Kay from Kelly Taxi were always available when we needed them. By the time we left we felt like they were family. Dawn and Dave were great at meeting us and orienting us to the features of the house. We had a fabulous time! Highly recommend Triton Overlook. We will be back!
10.0
Annual Family Vacation
We are blessed to visit a different paradise each year. Triton's was the best yet. The accommodations, views and service were A+. Dave & Dawn who manage the property are the best
10.0
Family of 6 with 4 young kids, highly recommends Triton's Overlook
We are a family with young kids ages 1, 4, 6, and 8. The stay was great and Dawn and Dave were very responsive to anything we needed or questions we asked. The kids all loved the beach and the pool. You can't beat the views and the location was excellent for quick trips to Red Hook. Overall we strongly recommend Triton's Overlook and will be back!
10.0
Perfect Location
Great house in a perfect location. Enjoyed our time on the island, the house was wonderful and had plenty of room to spread out.
10.0
Fabulous property1
We had a group of 8 long term friends celebrating our 60th birthday and Triton's outlook could not have been a more perfect place to stay! It is a gorgeous property with amazing views of the ocean, a beautiful swimming pool and hot tub! They provided beach towels, floats and even some snorkel gear (an unexpected bonus)
Joanne and Dave were great hosts, answering our many questions while planning our trip and also while we were there. The kitchen is well equipped with beautiful dishes, wine glasses, cookware which was great when we had a chef's dinner to celebrate. There are 3 beautiful living areas, including a media room. All 5 bedrooms have king size beds with four of them facing the ocean, which was great for our all adult crowd. Additionally it was very close to Red Hook and the ferry to St. John. Our favorite activity was a sunset sail on the Lady Lyndsey out of The Ritz Carlton, just a few minutes away. I would highly recommend this AMAZING property if you are planning to visit St. Thomas!!!
10.0
Excellent experience!
I cannot say enough wonderful things about Triton’s Overlook. The views from the house are breathtaking, the house is well maintained and the amenities and layout work very well for a large group (family and friends). The ability to walk to two nearby and beautiful beaches was so helpful to our group and made it such that we never wanted to leave! The kids and adults loved the pool and the hot tub, and the lower level media room was the perfect place for NCAA and movie watching while still feeling “outside.” Red Hook and its restaurants and stores and the ferries is only a 5 min drive away, and we frequented it often. Dawn and Dave were very accommodating as house managers and resolved any minor issues we had quickly. Joanne, the home owner, was very responsive to all pre-stay questions and certainly made us feel that our stay was important to her. We used the guest house as well as the main property and it provided more than ample room for a group of 13 to spread out and still never ever feel crowded. I would love to visit again!
10.0
Great vacation for 12
The property was beautiful! The views were gorgeous!
We had a great time enjoying the pool and hot tub!
10.0
Great Views and spacious
Our stay here was absolutely fabulous. The house is spacious and has numerous areas that can be used throughout the house. Everyone's favorite morning location was balcony off the main living room listening to the waves crash onshore and the beautiful view. The kitchen is spacious and has every utensil needed to cook large meals. The laundry room has 2 washers and 2 dryers to easily handle large amounts of laundry. Location is also conveniently located close to Red Hook area for groceries, restaurants, nightlife, beaches, boat excursions, and water recreation toys and vehicles to rent.
You will not be disappointed getting this house.
10.0
Great Week on STT and a super house
We had 4 couples for a week and all was good. Plenty of room in the house and a great pool area for cocktails in the evening.
Kitchen was good and spacious.
Only suggest more towels and possibly upgraded pillows. Small potatoes in the scheme of things.
We have been to the island many times and it’s the best place so far for a big group.
10.0
We felt like "Lives of the Rich and Famous"
For an active family, always exploring and on the move, this was the first time no one felt guilty about just hanging at The Triton. Our friend from Frenchtown did a lot of cooking for us and we dubbed the local supermarket "St. Moe's". Indoors was spacious and comfortable and outdoors was expansive and inviting. Such a memorable stay. Will go down in the family journal!
10.0
Fantastic
An amazing home in a great location.
10.0
Island Oasis
Triton’s Overlook is an amazing property with high end amenities throughout the house and some of the best views on the island. We were a group of 9 and you could easily never run into anyone in this sprawling estate. It is hard to decide if you want to spend your time on the private beach, in the pool or in the hot tub but you can't go wrong with any of those options. The snorkeling right in front of the house is the best on the island. I would highly recommend renting this property and we look forward to our next trip to this beautiful home!
10.0
You won't be disappointed
This property is stunning. Insane ocean views from the main living area and almost all bedrooms. Pool layout is amazing. Private beach . . excellent. It's an amazing home that checks all the boxes.
FAQs
How much does this house cost compared to others in Virgin Islands (U.S.)?
The average price for a rental in Virgin Islands (U.S.) is £364 per night. This rental is £925 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon. Enjoy the water!
Is Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Luxury Ocean Front Estate / Breathtaking Views/Private Beach and Lagoon?
We found 10 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and parking.
Explore similar vacation rentals in Virgin Islands (U.S.)
Explore all rentals in Virgin Islands (U.S.)Virgin Islands (U.S.) travel inspiration
Read our blogGuides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Guides
Top Things to Do in Fort Lauderdale, Florida
Guides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun