St. Thomas and St. John Luxury Vacations

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Flight and Luxury hotel deals in St. Thomas and St. John

Price found within the past 48 hours. Click for updated prices.
Point Pleasant Resort

Point Pleasant Resort

CA $1,767
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.6/10 Excellent! (1,000 reviews)
Great evening offerred to move us when there was local construction starting

Reviewed on Sep 8, 2026

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

CA $2,107
per person
Oct 29 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.6/10 Excellent! (1,501 reviews)
Sea Shore Allure

Sea Shore Allure

CA $4,262
per person
Nov 28 - Dec 5
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to St. Thomas (STT)
10/10 Exceptional! (47 reviews)
Our stay at Sea Shore Allure was amazing! The property is so clean and absolutely beautiful. The owners were so professional and accommodating. I truly cannot say enough about this special place! We will be staying here again when we return to St. John!

Reviewed on Aug 4, 2026

Secret Harbour Beach Resort

Secret Harbour Beach Resort

CA $2,492
per person
Oct 29 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9/10 Wonderful! (1,001 reviews)
The Westin St. John Resort Villas

The Westin St. John Resort Villas

CA $4,794
per person
Nov 28 - Dec 5
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to St. Thomas (STT)
8.4/10 Very good! (507 reviews)
Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!

Reviewed on Sep 12, 2026

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5* Luxury holidays in St. Thomas and St. John

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, St. Thomas

The Ritz-Carlton, St. Thomas

CA $3,961
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.4/10 Very good! (495 reviews)
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3 Night Luxury holidays in St. Thomas and St. John

Price found within the past 48 hours. Click for updated prices.
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

CA $2,365
per person
Dec 15 - Dec 18
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to St. Thomas (STT)
8.6/10 Excellent! (1,501 reviews)
Secret Harbour Beach Resort

Secret Harbour Beach Resort

CA $2,492
per person
Dec 15 - Dec 18
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to St. Thomas (STT)
9/10 Wonderful! (1,001 reviews)
Sea Shore Allure

Sea Shore Allure

CA $2,824
per person
Dec 15 - Dec 18
found 17 hours ago
Roundtrip flight included
Ottawa (YOW) to St. Thomas (STT)
10/10 Exceptional! (47 reviews)
Our stay at Sea Shore Allure was amazing! The property is so clean and absolutely beautiful. The owners were so professional and accommodating. I truly cannot say enough about this special place! We will be staying here again when we return to St. John!

Reviewed on Aug 4, 2026

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4 Night Luxury holidays in St. Thomas and St. John

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Windward Passage Hotel

Windward Passage Hotel

CA $1,557
per person
Oct 29 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
7.2/10 Good! (1,492 reviews)
The coffee in the room was ok. But the creamer was old like plastic and they need to up grade the sugar substitute with splender or equal And they need hand sanitizer in the rooms

Reviewed on Sep 27, 2026

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

CA $2,107
per person
Oct 29 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.6/10 Excellent! (1,501 reviews)
Two Sandals – A Boutique Hotel

Two Sandals – A Boutique Hotel

CA $1,982
per person
Oct 29 - Nov 2
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.8/10 Excellent! (519 reviews)
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Plan the perfect luxury St. Thomas and St. John vacation with Expedia

What are some benefits when booking luxury St. Thomas and St. John vacations?

When you book a luxury St. Thomas and St. John vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in St. Thomas and St. John?

If you're looking for something luxurious in St. Thomas and St. John, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,557, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 7. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in St. Thomas and St. John. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in St. Thomas and St. John?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout St. Thomas and St. John.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in St. Thomas and St. John. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in St. Thomas and St. John?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of St. Thomas and St. John or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in St. Thomas and St. John. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in St. Thomas and St. John

Sea Shore Allure

Sea Shore Allure

271 & 272 Fish Fry Drive St. John St John
  • 8 min drive from Sapphire Beach
Book a stay at this luxury hotel in St. John. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Sapphire Beach and Cruz Bay Beach are located ...
10/10 Exceptional! (47 reviews)
"Our stay at Sea Shore Allure was amazing! The property is so clean and absolutely beautiful. The owners were so professional and accommodating. I truly cannot say enough about this special place! We will be staying here again when we return to St. John!"

Reviewed on Aug 4, 2026

Sea Shore Allure
The Ritz-Carlton, St. Thomas

The Ritz-Carlton, St. Thomas

6900 Great Bay St. Thomas St. Thomas
  • 21 min walk from Sapphire Beach
Book a stay at this luxury resort in St. Thomas. Enjoy 2 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff in our reviews. ...
The Ritz-Carlton, St. Thomas
Infinity Villa

Infinity Villa

Skyline Drive St. Thomas
  • 10 min drive from Sapphire Beach
Book a stay at this luxury villa in St. Thomas. Enjoy free parking, private pools, and private hot tubs. Popular attractions Sapphire Beach and Magens Bay Beach ...
Infinity Villa
See all 3,972 properties in St. Thomas and St. John
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.

Things to do

Night Kayak Tour St. Thomas - Westin Frenchman's Reef

Night Kayak Tour St. Thomas - Westin Frenchman's Reef

CA $111
per adult
96% of travellers recommend
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
Guided Underwater Scooter and Snorkeling Activity in St. Thomas

Guided Underwater Scooter and Snorkeling Activity in St. Thomas

CA $184
per adult
100% of travellers recommend
Guided Underwater Scooter and Snorkeling Activity in St. Thomas
Sunset Sail with Cocktails and Appetizers

Sunset Sail with Cocktails and Appetizers

CA $133
per adult
98% of travellers recommend
Sunset Sail with Cocktails and Appetizers
See all activities in St. Thomas and St. John

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.