Estate Windsor holiday rentals

We found 776 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Estate Windsor that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as parking and a fireplace. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Estate Windsor

Showing deals for:20 Nov - 27 Nov

Living area
Exterior
Dining
Exceptional
(26 reviews)

St. Croix - Villa Views at Hermon Hill!

Christiansted

8% off
AU$8,803
for 7 nights, 1 villa
AU$1,258 per night
includes taxes & fees
St. Croix - Villa Views at Hermon Hill!
Exterior
Beach
Living area
Room
Exceptional
(11 reviews)

NEW! Private Apartment in Christiansted USVI

Christiansted

9% off
AU$1,889
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
NEW! Private Apartment in Christiansted USVI
Lush vegetation surrounding condo
View from living room
Another view from balcony
Interior
Wonderful
(12 reviews)

Beautiful Spacious Condo with Gorgeous Sea View

Christiansted

7% off
AU$1,412
for 7 nights, 1 apartment
AU$202 per night
includes taxes & fees
Beautiful Spacious Condo with Gorgeous Sea View
Dining
Property grounds
Bar (on property)
Living area
Exceptional
(6 reviews)

1 Br. "Sky View Suite" with private terrace

Christiansted

7% off
AU$1,689
for 7 nights, 1 villa
AU$241 per night
includes taxes & fees
1 Br. "Sky View Suite" with private terrace
Buck Island and Caribbean Blue Water!
The Landing at Cane Bay!
Dining
Queen Sized Bed
Very good
(6 reviews)

Hidden Treasure steps from The Botanical Gardens! Centrally located!

Grove Place

8% off
AU$1,135
for 7 nights, 1 apartment
AU$162 per night
includes taxes & fees
Hidden Treasure steps from The Botanical Gardens! Centrally located!
Fully equipped kitchen
Can`t beat the view from our unit!
Room
Ocean view from the primary suite
Exceptional
(24 reviews)

Puerta Azul

Christiansted

8% off
AU$2,687
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
Puerta Azul
Bathroom
Pool
Room
Private kitchen
Excellent
(17 reviews)

Caribbean Condo 3 With Pool with a View, and AC

Christiansted

8% off
AU$1,444
for 7 nights, 1 home
AU$206 per night
includes taxes & fees
Caribbean Condo 3 With Pool with a View, and AC
Dining
Pool
Private kitchen
Room
Exceptional
(35 reviews)

Condo with King Size Bed, near Downtown, with Ocean Views, AC, and Secured.

Christiansted

8% off
AU$1,444
for 7 nights, 1 apartment
AU$206 per night
includes taxes & fees
Condo with King Size Bed, near Downtown, with Ocean Views, AC, and Secured.
Kitchen
View from living room out French doors
Interior
View of North Shore
Exceptional
(113 reviews)

Amazing views from this Mid-Island Villa with swim up pool bar.

Christiansted

8% off
AU$3,925
for 7 nights, 1 villa
AU$561 per night
includes taxes & fees
Amazing views from this Mid-Island Villa with swim up pool bar.
Private kitchen
Pool
Private kitchen
Property grounds
Wonderful
(40 reviews)

Cliffside at Cane Bay - 3 bed/ 4 bath seaside home with private pool.

Kingshill

8% off
AU$6,318
for 7 nights, 1 villa
AU$903 per night
includes taxes & fees
Cliffside at Cane Bay - 3 bed/ 4 bath seaside home with private pool.
Fully equipped kitchen
Step into the vacation of a lifetime! - (Entrance) Living & Dining Room (open layout
Living & Dining Room (open layout) w/ Dry Bar - angle 2
Aerial view of Blue Paradise - just imagine what awaits you inside!
Exceptional
(7 reviews)

Blue Paradise Family Home

Christiansted

7% off
AU$8,714
for 7 nights, 1 home
AU$1,245 per night
includes taxes & fees
Blue Paradise Family Home
Private kitchen
Pool
Exterior
Terrace/patio
Excellent
(12 reviews)

Suite Dreams at Colony Cove - 2 bed / 2 bath seaside condo- beach and pool.

Christiansted

7% off
AU$2,254
for 7 nights, 1 apartment
AU$322 per night
includes taxes & fees
Suite Dreams at Colony Cove - 2 bed / 2 bath seaside condo- beach and pool.
Breeze on Inn has an unobstructed sea view !
Nothing but sea view here !
Dining area and breakfast bar
Tempt Lady Luck at the Casino...
Excellent
(58 reviews)

Breeze On Inn at Sugar Beach

Christiansted

7% off
AU$2,778
for 7 nights, 1 apartment
AU$397 per night
includes taxes & fees
Breeze On Inn at Sugar Beach
Open layout: Living Room, Kitchen & Dining Area - angle 1
Welcome to Island Oasis (front view)
Kitchen (w/additional dining seat)
Staircase leading to Jacuzzi
Exceptional
(5 reviews)

Island Oasis Family Home

Frederiksted

7% off
AU$5,990
for 7 nights, 1 home
AU$856 per night
includes taxes & fees
Island Oasis Family Home
Relax at our freshwater pool..sea side with direct beach access !
Located beachfront just west of Christiansted
Enjoy the sea view while you cook.
Direct beach access from the back gallery ( patio )
Exceptional
(61 reviews)

Toe's in the Sand-2 bed / 2 bath seaside condo - beach and pool.

Christiansted

7% off
AU$2,607
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Toe's in the Sand-2 bed / 2 bath seaside condo - beach and pool.
Exterior
Property grounds
Room
Private kitchen
Exceptional
(20 reviews)

A Quiet Retreat by the Sea

Christiansted

7% off
AU$2,052
for 7 nights, 1 apartment
AU$293 per night
includes taxes & fees
A Quiet Retreat by the Sea
Kitchen countertop and view into kitchen
View of ocean from the balcony
Condo complex from beach
Swimming lanes in pool
Exceptional
(23 reviews)

Delux Ocean Front 2 bed/2 bath fully furnished second floor condo.

Christiansted

7% off
AU$2,613
for 7 nights, 1 apartment
AU$373 per night
includes taxes & fees
Delux Ocean Front 2 bed/2 bath fully furnished second floor condo.
Private kitchen
Pool
Room
Exterior
Exceptional
(6 reviews)

Fan-Sea This at Sugar Beach

Christiansted

7% off
AU$2,778
for 7 nights, 1 apartment
AU$397 per night
includes taxes & fees
Fan-Sea This at Sugar Beach
Interior
Exterior
Property grounds
Room
Exceptional
(44 reviews)

Peaceful retreat located in Stoney Ground, minutes from Historic Frederiksted.

Frederiksted

8% off
AU$1,045
for 7 nights, 1 apartment
AU$149 per night
includes taxes & fees
Peaceful retreat located in Stoney Ground, minutes from Historic Frederiksted.
Pool view
Relaxation w/ a view!
Plush green lawn awaits you outside!
Aerial View of condominium complex
Exceptional
(97 reviews)

Serenity by the Sea, beautiful condo sleeps up to 4!

Christiansted

7% off
AU$2,799
for 7 nights, 1 apartment
AU$400 per night
includes taxes & fees
Serenity by the Sea, beautiful condo sleeps up to 4!
Breakfast bar and main living area A/C
Pool #2
All major appliances
Entry steps to the condo
Wonderful
(15 reviews)

Anchor's Away - 2 bed / 2 bath harbor view condo- beach and pool.

Christiansted

7% off
AU$2,316
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees
Anchor's Away - 2 bed / 2 bath harbor view condo- beach and pool.
The pool is seaside with direct beach access
Your view from Island Time !
Colony Cove is beachfront near Christiansted
Coral Sea Cafe is right next door at Mill Harbor
Excellent
(41 reviews)

Island Time - 2 bed / 2 bath seaside condo- beach and pool.

Christiansted

7% off
AU$2,293
for 7 nights, 1 apartment
AU$328 per night
includes taxes & fees
Island Time - 2 bed / 2 bath seaside condo- beach and pool.

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Book a holiday rental for your Estate Windsor getaway

Learn about the unique charm of Estate Windsor with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Estate Windsor

Do you want to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Estate Windsor a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Buccaneer Golf Course (6.3 mi / 10.1 km)
  • Carambola Golf Club (7.9 mi / 12.7 km)
  • The Reef Golf Course (10.8 mi / 17.3 km)
  • Carambola Golf Club (3 mi / 4.9 km)
  • Reef Golf Course (10.7 mi / 17.2 km)

Exploring the natural features in Estate Windsor

Whether you're an adventurous traveller or just want to appreciate the scenery, Estate Windsor is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Cane Bay (2.6 mi / 4.3 km)
  • Cane Bay Beach (2.7 mi / 4.3 km)
  • Sugar Beach (3.5 mi / 5.7 km)
  • Buccaneer Beach (5.8 mi / 9.4 km)
  • Shoys Beach (6.5 mi / 10.5 km)
  • Tamarind Reef Beach (7.5 mi / 12.1 km)

Travelling to and around Estate Windsor

The nearest airport is in Christiansted (SSB-St. Croix Seaplane Base), located 4.4 mi (7.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Christiansted (STX-Henry E. Rohlsen), which is 4.5 mi (7.3 km) away.

Frequently asked questions

What is the best area to stay in Estate Windsor when booking a holiday rental?
When considering a holiday rental in Estate Windsor, St. Croix Island, a highly recommended area to stay is the nearby Christiansted. This charming town is rich in history and offers a delightful blend of culture and leisure. You can explore the historic Danish buildings, such as the Old Danish Customs House, and take a leisurely stroll along the picturesque Boardwalk, where you'll find a variety of shops and restaurants with stunning views of the harbour.Additionally, the nearby Estate Whim Plantation Museum provides a fascinating insight into the island's sugar plantation history, making it a great spot for those interested in learning more about the local heritage. The Christiansted area boasts a range of holiday rentals, providing visitors with numerous options that cater to different tastes and budgets, ensuring a comfortable and enjoyable stay.
What are the top attractions in Estate Windsor?
Estate Windsor in St. Croix offers a variety of attractions that highlight the island's natural beauty and cultural heritage. Visitors can explore the nearby Sandy Point National Wildlife Refuge, a stunning area known for its pristine beaches and diverse wildlife, making it great for nature lovers. The historical town of Christiansted, not far from Estate Windsor, features well-preserved Danish historic architecture and attractions like Fort Christiansvaern and the Christiansted National Historic Site, providing a glimpse into the island's past.Additionally, the area is close to the vibrant local markets and eateries in downtown Christiansted, where visitors can enjoy delicious Caribbean cuisine and shop for local crafts.
Are all fees included in the Estate Windsor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Estate Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Estate Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Estate Windsor holiday homes?
You can find great discounts on holiday homes in Estate Windsor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Estate Windsor holiday home booking on Stayz?
To find Estate Windsor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Estate Windsor?
A long-stay holiday home in Estate Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Estate Windsor holiday home?
Book your Estate Windsor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Estate Windsor?
Prices for holiday homes in Estate Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Estate Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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