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Featured Villas in Estate Leinster Bay

Casa YaYa boasts stunning views, indoor/outdoor living and the perfect location!

10.0 out of 10, Exceptional, (154)
"We had an amazing time at the beautiful Casa YaYa! The view was incredible, especially with the full moon. The location was perfect for a more quiet getaway. We met some wonderful people at the local spots. Made it to Miss Lucy’s Thursday night for the live music and was such a blast! Highly recommend to future guests. Jeff and Maria were wonderful and were very quick to respond and inform us on a few road issues. Will be returning in the future when we visit our daughters in the islands! "
Casa YaYa boasts stunning views, indoor/outdoor living and the perfect location!

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

10.0 out of 10, Exceptional, (6)
"We loved our stay! We fished in the pond and snorkeled all over the island. Kids enjoyed all of the little extras. The hosts were very helpful!"
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

Scott Beach Villa #3

10.0 out of 10, Exceptional, (7)
"We were in awe of how easy the check in process was and how clean and spacious the apartment was. We were amazed at the view and close proximity to tourist attractions."
Scott Beach Villa #3

NEW Sleeps 17, POOL, and 3 mins to Hull Bay beach!

2.0 star property
NEW Sleeps 17, POOL, and 3 mins to Hull Bay beach!

Villa Marina Vista

4.0 star property
9.6 out of 10, Exceptional, (36)
"Pros: beautiful apartment with a spectacular view of the ocean and harbor. Comfortable beds and furniture and a balcony that was like a gateway to heaven. The host was friendly and happy to help. Had many unexpected extras like beach towels, sunscreen and an XBox. Cons: getting to the apartment was like climbing a very crumbly road to the top of Mt. Everest. It was not easy to get to and the cab drivers took full advantage of the fact that the climb up was difficult on foot and charged an arm...
Villa Marina Vista

HEAVENLY VIEWS and PRIVATE POOL!!

10.0 out of 10, Exceptional, (144)
"We had an amazing stay at Villa Celeste! The views are absolutely amazing! The size was perfect for the two of us for our honeymoon. Joy was so responsive and incredible! Coral bay is a nice peaceful retreat away from the noise of Cruz Bay! Don’t forget your jeep rental. It was a honeymoon we won’t ever forget! "
HEAVENLY VIEWS and PRIVATE POOL!!

Calichi at Picture Point

4.0 star property
9.8 out of 10, Exceptional, (63)
"A very special place. Amazing property with a view like no other. We stayed in papaya (hot tub on the roof). The place is well equipped and absolutely perfect, they even had beach chairs and a cooler to borrow. I can’t imagine staying at any other place in St John."
Calichi at Picture Point

BEACHFRONT LUXURY at the Ritz!! We own TWELVE residences, MOST DATES Available!!

9.8 out of 10, Exceptional, (74)
"See Trip Advisor for full review"
The price is AU$1,815
includes taxes & fees
1 Dec - 2 Dec
BEACHFRONT LUXURY at the Ritz!! We own TWELVE residences, MOST DATES Available!!

Vessup View · 5BR -Walk to the beach! Close to the Ritz Carlton!

10.0 out of 10, Exceptional, (7)
"The house is great for a group wanting space to spread out. Neighborhood seemed nice enough, roads on the island are small & not great for walking so a rental car is helpful. AC units in all of the bedrooms which was great. We did find the hot water was not consistent so we took many cold showers. They have beach chairs for you to take when you venture to many of the beaches, however they didn’t have much for other pool/beach equipment. Only a few beach towels. Pool is large enough for a few...
Vessup View · 5BR -Walk to the beach! Close to the Ritz Carlton!

Miles Away, 2 BR 2.5 BA. The perfect private getaway for couples or families!

10.0 out of 10, Exceptional, (66)
"This was our first time visiting St. John, but it will certainly not be our last. Miles Away was the ideal place to be on the island in my opinion. It was secluded and serene, yet still close to Cruz Bay and the excursions we were interested in within the National Park. The space was exactly what you would think of when imagining a hillside villa in a tropical paradise. It was a great size for our family of 4 as well. The pool was likely our favorite spot in the house as it overlooks the bay...
Miles Away, 2 BR 2.5 BA. The perfect private getaway for couples or families!

Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views

9.8 out of 10, Exceptional, (71)
"Everything was perfect at Villa Capiz! The house was filled with everything we needed for a stress-free rental. Beach towels, coolers, beach chairs, even stainless steel cups with lids! The owners were super helpful leading up to the week and throughout. They have contacts for everything! Taxis, boat rentals, jeep rentals… you name it. We will absolutely be back as soon as we can! "
Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views

St Thomas Cliffside Villa with Pool & Hot Tub!

9.4 out of 10, Exceptional, (55)
"This place in this place! I don’t know what I liked more, the house itself, which is so charming and conveniently stocked with anything you might need on your trip to St. Thomas. Or the view from the place, which seems to change throughout the day, revealing a new islands we hadn’t seen before. It’s dream-inducing. Or is it St. Thomas? I feel in love with that island and its people. Honestly I would stay anywhere and love the island but if you want to do it nice, you won’t regret booking this...
St Thomas Cliffside Villa with Pool & Hot Tub!

Searenity Villa in Cruz Bay with private pool and sunset view

10.0 out of 10, Exceptional, (11)
"Wow! First off the view is amazing. We were expecting a good view from the pictures online but they don’t do it justice. Stunning sunsets setting over islands every night. The kitchen is amazing with a huge island that was perfect for us as we cooked a lot and the kitchen had all the amenities. There was a constant cross-breeze that kept us very comfortable. The bedroom has a separate sitting area that is perfect for working remotely and had an air conditioner that made the room very...
The price is AU$1,733
includes taxes & fees
17 Dec - 18 Dec
Searenity Villa in Cruz Bay with private pool and sunset view

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

9.4 out of 10, Exceptional, (19)
"We loved the view and the location of this spectacular rental. The only drawback was the mosquitos getting in and biting us. It would be wonderful if you could screen the doors out to the patio to keep them out or install HVAC in the main area!"
The price is AU$1,832
includes taxes & fees
4 Dec - 5 Dec
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

Luxurious Caribbean Suite -4

8.0 out of 10, Very good, (5)
"We had such a great time staying at this studio in the heart of Cruz Bay. The description and pictures of the property are very accurate. Check-in was a breeze, and the owner was extremely responsive. We were able to walk to everything. We rented a car to explore the East End on our own, but I could see staying here without one as it is really close to EVERYTHING, including taxis to north side beaches. We chose to bring in food and cook to save some money. The studio wasn't as well equipped to...
The price is AU$717
includes taxes & fees
2 Dec - 3 Dec
Luxurious Caribbean Suite -4

Stunning views! Infinity pool. 5* South Shore home.

10.0 out of 10, Exceptional, (102)
"Loved the property. Great view and convenient location (12 min from Cruz Bay). 4 great master suites, gorgeous pool and wonderful kitchen. Friendly and helpful property manager. Thank you!"
Stunning views! Infinity pool. 5* South Shore home.

Sweeping view of Magens Bay & Tropical Lagoon Pool

10.0 out of 10, Exceptional, (50)
"Nice cozy place with plenty of accomodations "
Sweeping view of Magens Bay & Tropical Lagoon Pool

Private Paradise! One level, panoramic views from every room!

10.0 out of 10, Exceptional, (121)
"Great, well equipped, house, quiet location, beautiful views! Southern side of the island provided sun on the pool all day and sunset views in the evening. "
Private Paradise! One level, panoramic views from every room!

Million Dollar Views: Walk to Beach, Pools, and Restaurant

9.6 out of 10, Exceptional, (181)
"We spent a week at Pleasant Point Resort and found it to be a perfect spot. We visited locations all over the island and even when it was raining, it was so spectacular we simply paused and enjoyed the breathtaking setting we used as home base!"
The price is AU$648
includes taxes & fees
29 Dec - 30 Dec
Million Dollar Views: Walk to Beach, Pools, and Restaurant

NEWLY RENOVATED Private Beach Views, Luxury Villa Milagro - Villa 4

10.0 out of 10, Exceptional, (37)
"Beautiful property with very nice view."
NEWLY RENOVATED Private Beach Views, Luxury Villa Milagro - Villa 4
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Estate Leinster Bay

Hilltop Villas at Bluebeard's Castle by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (1362)
"The location is near everything or minutes away "
The price is AU$345
includes taxes & fees
11 Dec - 12 Dec
Hilltop Villas at Bluebeard's Castle by Capital Vacations

Castle Villas at Bluebeard's by Capital Vacations

2.5 star property
8.4 out of 10, Very good, (892)
"Everything was at your fingertips. Amazing property."
The price is AU$271
includes taxes & fees
1 Dec - 2 Dec
Castle Villas at Bluebeard's by Capital Vacations

Flamboyan on the Bay Resort and Villas

3.5 star property
8.8 out of 10, Excellent, (513)
"Had a great time and the staff were extremely friendly and helpful. "
The price is AU$214
includes taxes & fees
14 Dec - 15 Dec
Flamboyan on the Bay Resort and Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.