Estate Dorothea Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Estate Dorothea holiday rentals

Aerial view
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Condo in St. Thomas

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
9.4 out of 10, Exceptional, (223)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is HK$156
HK$1,536 total
includes taxes & fees
30 Dec - 31 Dec
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
Beach nearby, sun-loungers, beach towels
Lameshur Bay Glamping Site with AC

Camping in St John

Lameshur Bay Glamping Site with AC
10.0 out of 10, Exceptional, (24)
"The location is amazing, the space was clean, and the kitchen area, shower, and snorkeling/beach gear were much appreciated!"
United States
Ann
The price is HK$1,113
HK$1,913 total
includes taxes & fees
31 Dec - 1 Jan 2026
Lameshur Bay Glamping Site with AC
Exterior
Flamboyan on the Bay Resort and Villas

Condo resort in St. Thomas

Flamboyan on the Bay Resort and Villas
3.5 star property
8.6 out of 10, Excellent, (807)
"location nice pool "
United States
Gary
The price is HK$1,254
HK$1,537 total
includes taxes & fees
4 Jan - 5 Jan 2026
Flamboyan on the Bay Resort and Villas
Beach nearby
Lameshur Cottage's Guest House

Cottage in St John

Lameshur Cottage's Guest House
10.0 out of 10, Exceptional, (133)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is HK$2,061
HK$3,501 total
includes taxes & fees
25 Jan - 26 Jan 2026
Lameshur Cottage's Guest House
Property entrance
The Landmark Apartment

Aparthotel in St. Thomas

The Landmark Apartment
2.5 star property
8.8 out of 10, Excellent, (15)
"I loved the historic nature of the building. It had an interesting layout, but it was very spacious and clean, and had a wonderful location for walking around downtown and seeing the sights."
United States
Mercy
The price is HK$1,693
HK$3,072 total
includes taxes & fees
28 Dec - 29 Dec
The Landmark Apartment
Exterior
Villa Island Paradise

Villa in St. John

Villa Island Paradise
4.0 star property
9.2 out of 10, Wonderful, (7)
"Very safe and secure place! Also very clean! Just uphill from cruz bay "
United States
Tyler
The price is HK$1,190
HK$5,958 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Island Paradise
Terrace/patio
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Apartment in St Thomas

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
10.0 out of 10, Exceptional, (39)
"Clean home, accurate check-in instructions, splendid view!"
United States
Jeffrey
The price is HK$995
HK$1,921 total
includes taxes & fees
11 Jan - 12 Jan 2026
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
Beach nearby
Family Glamping Site with AC

Camping in St John

Family Glamping Site with AC
10.0 out of 10, Exceptional, (30)
"Overall great property only semi complaint which is more needy than anything is the tent will get a bit stuffy and hot when the fans die. "
United States
Will C.
The price is HK$1,253
HK$2,094 total
includes taxes & fees
31 Dec - 1 Jan 2026
Family Glamping Site with AC
Terrace/patio
Salt Pond Bay Glamping Site With AC

Camping in St John

Salt Pond Bay Glamping Site With AC
The price is HK$1,043
HK$1,850 total
includes taxes & fees
31 Dec - 1 Jan 2026
Salt Pond Bay Glamping Site With AC
Fridge, microwave, stovetop, coffee/tea maker
Zoë Oasis - The Couple’s Choice & #1 Wholesome Getaway 🤍

Apartment in St Thomas

Zoë Oasis - The Couple’s Choice & #1 Wholesome Getaway 🤍
10.0 out of 10, Exceptional, (17)
"The mountain top view was fantastic and the hosts were very kind and accommodating. I would definitely return and advocate to stay here for anyone visiting the VI's. "
United States
Rene R.
The price is HK$1,089
HK$2,702 total
includes taxes & fees
9 Jan - 10 Jan 2026
Zoë Oasis - The Couple’s Choice & #1 Wholesome Getaway 🤍
Terrace/patio
The Breeze St Thomas

Aparthotel in St. Thomas

The Breeze St Thomas
2.0 star property
The price is HK$2,187
HK$3,846 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Breeze St Thomas
Private kitchen
Little Indigo Apartments

Apartment in St. Thomas

Little Indigo Apartments
3.5 star property
8.4 out of 10, Very good, (22)
"Amazing views, very nice people"
United States
Ramie
The price is HK$1,498
HK$2,612 total
includes taxes & fees
1 Jan - 2 Jan 2026
Little Indigo Apartments
Fridge, microwave, oven, stovetop
Eagles Nest Near the Beach

Apartment in St Thomas

Eagles Nest Near the Beach
9.8 out of 10, Exceptional, (22)
"Great spot, great host. Albert was super helpful "
United States
McRae W.
The price is HK$805
HK$1,785 total
includes taxes & fees
6 Jan - 7 Jan 2026
Eagles Nest Near the Beach
On the beach
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

Villa in Maho Bay Quarter

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
9.6 out of 10, Exceptional, (27)
"Beautiful property with gorgeous views! Tommy was very quick to answer any questions or just give us information!"
United States
Amy G.
The price is HK$6,959
HK$11,171 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
Terrace/patio
Shibui Cove

Apartment in St. Thomas

Shibui Cove
2.0 star property
10.0 out of 10, Exceptional, (1)
"I had a great stay here. The view was absolutely stunning. Being up on the side of the mountain was great. Very private but less than 5 min away from town. I will definitely stay again. "
United States
Adam R
The price is HK$1,470
HK$2,967 total
includes taxes & fees
1 Jan - 2 Jan 2026
Shibui Cove
Outdoor dining
The Villa Michelle • Luxury • Heated Pool • Generator

Villa in St Thomas

The Villa Michelle • Luxury • Heated Pool • Generator
2.0 star property
10.0 out of 10, Exceptional, (8)
"Loved this place had an amazing time. Kinda far from everything so be prepared to pay big buck for rides. Luckily the house property manager was able to take us to the store and back to the house with no hesitation. The view on the balconies was so beautiful and perfect! "
United States
Shontecia
The Villa Michelle • Luxury • Heated Pool • Generator
Beach nearby
Stylish Beach Condo located on Sapphire Beach

Condo in Smith Bay

Stylish Beach Condo located on Sapphire Beach
8.8 out of 10, Excellent, (18)
"Let renter know bed is raised and need to step down to get to floor. A bit of a surprise. "
United States
stuart
The price is HK$1,470
HK$2,657 total
includes taxes & fees
6 Jan - 7 Jan 2026
Stylish Beach Condo located on Sapphire Beach
Terrace/patio
Sophisticated Beach Condo-Ocean View-Sapphire

Holiday Home in Smith Bay

Sophisticated Beach Condo-Ocean View-Sapphire
9.0 out of 10, Wonderful, (32)
"Me and my gf’s loved staying here! Best part was having close beach access! "
United States
Maria
The price is HK$1,314
HK$2,450 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sophisticated Beach Condo-Ocean View-Sapphire
View from property
Suite St. John at Gallows Point Resort

Aparthotel in St. John

Suite St. John at Gallows Point Resort
4.0 star property
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is HK$6,182
HK$8,430 total
includes taxes & fees
11 Jan - 12 Jan 2026
Suite St. John at Gallows Point Resort
Interior
Single Night Bookings Welcome - Tropical Modern Loft - SoHo Style - Concierge

Holiday Home in Charlotte Amalie

Single Night Bookings Welcome - Tropical Modern Loft - SoHo Style - Concierge
10.0 out of 10, Exceptional, (8)
"Nice loft with a great library in downtown Charlotte Amelie. Loved the stay, will go back if I am in the area."
United States
Kevin S.
The price is HK$5,435
HK$7,270 total
includes taxes & fees
1 Jan - 2 Jan 2026
Single Night Bookings Welcome - Tropical Modern Loft - SoHo Style - Concierge
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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Top Estate Dorothea Hotel Reviews

Windward Passage Hotel

Windward Passage Hotel

10/10 Excellent
"Customer service "
LaVern 5-night trip
Posted 2 days ago
Windward Passage Hotel

Find out more about Estate Dorothea

Search for holiday rentals in Estate Dorothea on Expedia! You can easily find your home rentals, villas, holiday apartments in Estate Dorothea using one of the methods below:

  • View our selection of featured holiday rentals in Estate Dorothea
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Look no further and take a look at our great range of rental properties in Estate Dorothea!

Frequently asked questions

Can I find a holiday rental in Estate Dorothea?

Yes, there are holiday rentals close to the most popular sights in Estate Dorothea, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Estate Dorothea has to offer?

The Cottage at Villa Indigo: This holiday home rental outside of Estate Dorothea is located in the mountains, and offers a private garden, Netflix and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What’s there to see and do in Estate Dorothea?

Get outdoors into nature at a spot like Sapphire Beach, or visit other top attractions such as Trunk Bay. Lindbergh Bay and Magens Bay are a couple of places you'll find in the wider area.

What’s a holiday rental in Estate Dorothea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Dorothea. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.