Estate Windsor Holiday Rentals

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Our top choices for Estate Windsor holiday rentals

10.0 out of 10, Exceptional, (2)
"The location was just perfect with a 9 hole golf course, Ollie’s a terrific quick breakfast/lunch place and Duggins one of the best restaurants on the island. The owners are very responsive and friendly. The views are magnificent. I wouldn’t stay anywhere else."
United States
Lou S.
Beautiful 2-bd condo w/ views walking distance to beach in amazing Christiansted

Aparthotel in Christiansted Historic District

Historic Apt in Heart of Christiansted
3.5 star property
9.4 out of 10, Exceptional, (17)
"Excellent location "
United States
Brian G
The price is NZ$433
includes taxes & fees
25 Jan - 26 Jan 2026
Historic Apt in Heart of Christiansted

Holiday Home in Christiansted Historic District

The Crucian Queen - AC - Walkable
2.0 star property
The price is NZ$896
includes taxes & fees
5 Jan - 6 Jan 2026
The Crucian Queen - AC - Walkable
9.4 out of 10, Exceptional, (63)
"Wonderful stay. Accomodating host."
United States
Alex G.
The price is NZ$278
includes taxes & fees
30 Dec - 31 Dec
STUDIO APT. a/c - stable wifi - filtered tap water - 5 min. to the boardwalk
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. Host was very responsive and condo was great! Great location too!"
United States
christine b.
The price is NZ$979
includes taxes & fees
28 Dec - 29 Dec
2 Bedroom Sleeps 6 - Cozy Condo with beach access
8.6 out of 10, Excellent, (69)
"LllIt was cool once the air condition was finally fixed"
United States
Danielle B.
The price is NZ$593
includes taxes & fees
10 Jan - 11 Jan 2026
Luxe Condo On the Beach: Pool, Hot Tub + FREE WiFi

Holiday Home in Christiansted Historic District

The Queen’s Quarters- King Suite - AC - Walkable
2.0 star property
The price is NZ$1,147
includes taxes & fees
7 Jan - 8 Jan 2026
The Queen’s Quarters- King Suite - AC - Walkable
10.0 out of 10, Exceptional, (14)
"Clean and excellent stay. Service was above and beyond"
United States
Cole S.
The price is NZ$377
includes taxes & fees
17 Jan - 18 Jan 2026
Lovely 1-bedroom condo with Fresh Water Pool
9.6 out of 10, Exceptional, (13)
"Beautiful view, very close to beaches, overall it was a great stay."
United States
Nelicia N.
The price is NZ$360
includes taxes & fees
9 Jan - 10 Jan 2026
Sunset Villas "Good Morning" Tiny Home Container
9.2 out of 10, Wonderful, (18)
"great place in st. croix. Our host Russell made it very easy and accommodating"
United States
jeffrey b.
The price is NZ$537
includes taxes & fees
28 Dec - 29 Dec
Your Caribbean home away from home

Cottage in Christiansted

Romey's Villa in Gated Community
10.0 out of 10, Exceptional, (1)
"Location is great, close to Christiansted for shopping and restaurants, and the Buccaneer Hotel & Golf Resort and my favorite - Shoy's beach. Comfortable bed. Safe gated neighborhood."
United States
Janel F.
The price is NZ$599
includes taxes & fees
7 Jan - 8 Jan 2026
Romey's Villa in Gated Community
The price is NZ$586
includes taxes & fees
26 Dec - 27 Dec
All new King suite on the North Shore with access to marketplace and pool
8.8 out of 10, Excellent, (8)
"Nice quiet place to stay in a great walking neighborhood. Nice central location."
United States
Anthony B.
The price is NZ$341
includes taxes & fees
4 Jan - 5 Jan 2026
Large & Comfortable 1 Bed/Bath Guest Room on St. Croix
10.0 out of 10, Exceptional, (1)
"It is a lovely home. The property is immaculate and it was very smooth no complaints. The home owner is a pleasant and kind man. I highly recommend a stay here. You will not be disappointed "
United States
Benjamin C.
The price is NZ$1,164
includes taxes & fees
28 Dec - 29 Dec
Tranquil Buck Island Views - Steps from the Beach
8.6 out of 10, Excellent, (14)
"Great stay "
United States
Andrew
The price is NZ$1,062
includes taxes & fees
31 Dec - 1 Jan 2026
Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA
2.0 star property
10.0 out of 10, Exceptional, (3)
"Their property was very nice and clean and loved the area where it was located at"
United States
Stephen M T.
The price is NZ$708
includes taxes & fees
30 Dec - 31 Dec
"Spectacular Ocean Views" at Calypso Castillo!
The price is NZ$315
includes taxes & fees
3 Jan - 4 Jan 2026
A safe, family friendly bird watchers paradise with a beautiful ocean view.
10.0 out of 10, Exceptional, (1)
"Didn't stay there but the host was very courteous "
United States
Gary
The price is NZ$690
includes taxes & fees
26 Dec - 27 Dec
Island Life#2 @Bay Garden Live Local. GOOD PRICE!!Clean with Ocean views

Apartment in Christiansted Historic District

Queen's Promise - King Suite - AC - Walkable
2.0 star property
The price is NZ$977
includes taxes & fees
5 Jan - 6 Jan 2026
Queen's Promise - King Suite - AC - Walkable
10.0 out of 10, Exceptional, (60)
"Friendly hosts, amazing view. Would definitely stay here again!"
United States
Amy E.
The price is NZ$958
includes taxes & fees
8 Jan - 9 Jan 2026
St.Croix, USVI- Cane Bay Beach -direct waterfront Cottage!
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 Windsor Hotel Reviews

Find out more about Estate Windsor

Everything you need to know about Estate Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Estate Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Estate Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Estate Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Estate Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Estate Windsor holiday rentals we have selected for you start as low as NZ$433 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Estate Windsor rentals

At Expedia, we put the best Estate Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Estate Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Estate Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Estate Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Estate Windsor?

Yes, there are holiday rentals close to the most popular sights in Estate Windsor, 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 Windsor has to offer?

Sugar Apple Bed & Breakfast: This holiday home rental outside of Estate Windsor is located near the airport, and has an outdoor pool, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities such as a microwave and an electric kettle can make your holiday run smoothly. Make the most of garden in this rental home to help you unwind.

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

While you're exploring the area, Cane Bay and Cane Bay Beach are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Carambola Golf Club and Sugar Beach.

What’s a holiday rental in Estate Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Windsor. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get 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 small group gathering.