
Estate Contant Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Estate Contant Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

The Breeze
Price was $1,558, price is now $1,311 per person
$1,311
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to St. Thomas (STT)
Stay at this aparthotel in St. Thomas. Enjoy free WiFi, free parking, and 9 outdoor pools. Popular attractions Sapphire Beach and Magens Bay Beach are located nearby.

Villa Island Paradise
Price was $5,364, price is now $3,633 per person
$3,633
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to St. Thomas (STT)
Book a stay at this business-friendly villa in St. John. Enjoy free WiFi, free parking, and a garden. Popular attractions Virgin Islands National Park and Sapphire Beach are located nearby.
St. Thomas is prone to blackouts. During our stay we experienced one which left us without AC in a very hot destination. This villa does not have a back up generator for when the power goes out. Outside of that this place was great and the owners were responsive when we contacted them. All other amenities were taken care of even beach chairs, cooler, beach umbrella, and some snorkeling gear!
Reviewed on Nov 13, 2026

At Home in the Tropics
Price was $2,150, price is now $1,734 per person
$1,734
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to St. Thomas (STT)
Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Magens Bay Beach and Sapphire Beach are located nearby.
The view as you can see cruise ships at the port as well as a beautiful ocean. Room is small but comfortable. TV doesn’t work, no connection at all to any channels. No parking, No Balcony. If you have no rental vehicle, good luck of walking them stairs back to the property.
Reviewed on Nov 1, 2026

Margaritaville Vacation Club - St. Thomas
Price was $2,819, price is now $2,281 per person
$2,281
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to St. Thomas (STT)
Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sapphire Beach and Coki Point Beach are located nearby.

The Westin St. Thomas Beach Resort & Spa
Price was $3,715, price is now $3,100 per person
$3,100
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to St. Thomas (STT)
Book a stay at this luxury resort in St. Thomas. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sapphire Beach and Bolongo Bay are located nearby.
The staff experience was mixed. While some employees were helpful, the overall service was fairly minimal and did not go beyond the bare minimum.
On the other hand, there were 2 food servers at Luna Mar Restaurant - Crystal and Pablo, they were absolutely wonderful! They were outstanding, attentive, genuinely helpful, and made our dining experience that much more enjoyable. Good vibes! And very funny! They truly stood out!
The food was amazing too
Reviewed on Nov 14, 2026

The Cottage at Villa Indigo
Price was $1,865, price is now $1,594 per person
$1,594
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to St. Thomas (STT)
Stay at this vacation home in St. Thomas. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Sapphire Beach and Magens Bay Beach are located nearby.
We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back
Reviewed on May 26, 2025
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Bluebeard's Castle Resort
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
14.05 km from city center
Stay at this aparthotel in St. Thomas. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Magens Bay Beach and Sapphire Beach ...

The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
13.72 km from city center
Book a stay at this luxury resort in St. Thomas. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean ...

Margaritaville Vacation Club - St. Thomas
6080 Estate Smith Bay St. Thomas
8.43 km from city center
Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular ...

Bunker Hill Hotel
2307 Commandant Gade St. Thomas
14.83 km from city center
Stay at this hotel in St. Thomas. Enjoy free WiFi, daily housekeeping, and cable TV channels. Our guests praise the breakfast and the pool in our reviews. Popular ...

Windward Passage Hotel
Veterans Drive Charlotte Amali St. Thomas St. Thomas
15.39 km from city center
Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...

Emerald Beach Resort
8070 Lindbergh Bay St. Thomas St. Thomas
18.18 km from city center
Book a stay at this beach hotel in St. Thomas. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our ...

The Ritz-Carlton, St. Thomas
6900 Great Bay St. Thomas St. Thomas
5.45 km from city center
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. ...

Lindbergh Bay Hotel and Villas
8075 Lindbergh Bay St. Thomas St. Thomas
18.8 km from city center
Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...

The Westin St. John Resort Villas
300B Chocolate Hole St. John
0.69 km from city center
Book a stay at this luxury aparthotel in St. John. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Virgin Islands National Park and ...

Buoy Haus Beach Resort St. Thomas, Autograph Collection
2 Estate Bakkeroe St. Thomas VI
13.52 km from city center
Book a stay at this business-friendly hotel in St. Thomas. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Popular attractions Magens Bay Beach and Sapphire ...

Mafolie Hotel
7091 Estate Mafolie St. Thomas
14.97 km from city center
Stay at this hotel in St. Thomas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

Hampton by Hilton St. Thomas
Havensight Mall Parcel 2 Charlotte Amalie St. Thomas
13.69 km from city center
Stay at this hotel in St. Thomas. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sapphire Beach and Magens Bay Beach are located ...

Bolongo Bay Beach Resort
7150 Bolongo St. Thomas St. Thomas
11.22 km from city center
Stay at this resort in St. Thomas. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 9 - Wed, Feb 10
MIA
Miami Intl.
STT
Cyril E. King
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago

Wed, Jan 13 - Tue, Jan 19
JFK
John F. Kennedy Intl.
STT
Cyril E. King
$377 Roundtrip, found 21 hours ago
$377
Roundtrip
found 21 hours ago

Tue, Feb 9 - Wed, Feb 10
MIA
Miami Intl.
STT
Cyril E. King
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago

Tue, Jan 5 - Tue, Jan 26
BOS
Logan Intl.
STT
Cyril E. King
$410 Roundtrip, found 3 days ago
$410
Roundtrip
found 3 days ago

Mon, Dec 7 - Thu, Dec 17
EWR
Newark Liberty Intl. Airport
STT
Cyril E. King
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago

