Book Holiday Homes in Saint James Windward Parish

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Saint James Windward Parish

Stunning Caribbean House With Breath-taking Views

Stunning Caribbean House With Breath-taking Views

Turtle Beach Saint George Basseterre Parish
When you stay at this vacation home in Basseterre, you'll be on the beach, within a 5-minute drive of Cockleshell Bay and Banana Bay Beach.
Opens in a new windowStunning Caribbean House With Breath-taking Views
#3-2BR Shalimar Vacation Townhouse, Frigate Bay, Saint Kitts.

#3-2BR Shalimar Vacation Townhouse, Frigate Bay, Saint Kitts.

Basseterre Saint George Basseterre Parish
Located in Basseterre, this vacation home is in the mountains, within a 5-minute drive of Frigate Bay Beach and Timothy Hill.
Opens in a new window#3-2BR Shalimar Vacation Townhouse, Frigate Bay, Saint Kitts.
Turtle beach White House(3)luxury romantic cottage

Turtle beach White House(3)luxury romantic cottage

Basseterre Southeast peninsula
When you stay at this vacation home in Basseterre, you'll be on the beach, within a 5-minute drive of Cockleshell Bay and Banana Bay Beach.
Opens in a new windowTurtle beach White House(3)luxury romantic cottage
Save an average of 15% on thousands of hotels when you're signed in
Cozy Romantic Bungalow  — 3 min walk to the beach, in front of the golf course!

Cozy Romantic Bungalow — 3 min walk to the beach, in front of the golf course!

Frigate Bay St. Kitts
With a stay at this vacation home in Basseterre, you'll be within a 10-minute walk of Frigate Bay Beach and Frigate Bay.
Opens in a new windowCozy Romantic Bungalow — 3 min walk to the beach, in front of the golf course!
Private romantic retreat, ideally located, panoramic views, walk to the beach.

Private romantic retreat, ideally located, panoramic views, walk to the beach.

Cades Bay Nevis
Located in Westbury, this vacation home is within a 5-minute drive of Pinney's Beach and Oualie Beach.
Opens in a new windowPrivate romantic retreat, ideally located, panoramic views, walk to the beach.
Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!

Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!

Basseterre Caribbean
When you stay at this vacation home in Basseterre, you'll be by the ocean, within a 5-minute drive of Cockleshell Bay and Banana Bay Beach.
Opens in a new windowLuxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!
Caribbean Ocean View Home

Caribbean Ocean View Home

Frigate Bay, Basseterre St. Kitts
When you stay at this vacation home in Basseterre, you'll be near the beach, within a 15-minute walk of Frigate Bay and Frigate Bay Beach.
Opens in a new windowCaribbean Ocean View Home
Mango Delight - 3 bedroom Caribbean Vacation Home

Mango Delight - 3 bedroom Caribbean Vacation Home

New Castle Village, St. James Parish Nevis
When you stay at this vacation home in Newcastle, you'll be near the airport, within a 5-minute drive of Cottle Church and Cat Ghaut Chip 'n Putt.
Opens in a new windowMango Delight - 3 bedroom Caribbean Vacation Home
ST KITTS 'Turtle Nest' At Turtle Beach,  A Comfortable Two Bedroom Apartment

ST KITTS 'Turtle Nest' At Turtle Beach, A Comfortable Two Bedroom Apartment

Turtle Beach Saint George Basseterre Parish
Located in Basseterre, this vacation home is by the sea, within a 5-minute drive of Cockleshell Bay and Banana Bay Beach.
Opens in a new windowST KITTS 'Turtle Nest' At Turtle Beach, A Comfortable Two Bedroom Apartment
Don't see what you're looking for?
See all available properties in Saint James Windward Parish
View all properties
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.

Saint James Windward Parish Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Saint James Windward Parish vacation homes are the perfect way for you to wing it.

Holiday houses in Saint James Windward Parish let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Saint James Windward Parish in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Saint James Windward Parish adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Saint James Windward Parish with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Saint James Windward Parish vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Saint James Windward Parish Holiday Homes essential information

Accommodation
47 Holiday Homes
Lowest Price
AU$203
Highest Price
AU$476
Popular accommodation
Stunning Caribbean House With Breath-taking Views, #3-2BR Shalimar Vacation Townhouse, Frigate Bay, Saint Kitts., Turtle beach White House(3)luxury romantic cottage, Cozy Romantic Bungalow — 3 min walk to the beach, in front of the golf course!, Private romantic retreat, ideally located, panoramic views, walk to the beach. , Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!, Caribbean Ocean View Home, Mango Delight - 3 bedroom Caribbean Vacation Home, ST KITTS 'Turtle Nest' At Turtle Beach, A Comfortable Two Bedroom Apartment

Top trending hotels in Saint James Windward Parish

Oualie Beach Resort

Oualie Beach Resort

3 out of 5
Oualie Beach Newcastle Nevis
Fully refundableReserve now, pay when you stay
With a stay at Oualie Beach Resort in Newcastle, you'll be on the beach, just steps from Oualie Beach and a 4-minute drive from Cottle Church.
Opens in a new windowOualie Beach Resort
Mount Nevis Hotel

Mount Nevis Hotel

4 out of 5
Shaws Road Newcastle Nevis
The price is AU$476 per night from 16 Jan to 17 Jan
AU$476
16 Jan - 17 Jan 2026
includes taxes & fees
Located in Newcastle, Mount Nevis Hotel is a 4-minute drive from Cottle Church and 5 minutes from St Thomas Anglican Church.
Opens in a new windowMount Nevis Hotel
Calypso Hotel Nevis

Calypso Hotel Nevis

2 out of 5
Potwork Camps
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 17 Dec to 18 Dec
AU$203
17 Dec - 18 Dec
includes taxes & fees
Located in Camps, Calypso Hotel Nevis is a 5-minute drive from Windward Sands Beach and 7 minutes from Eden Brown Estate.
Opens in a new windowCalypso Hotel Nevis
Save an average of 15% on thousands of hotels when you're signed in
Mango Delight - 3 bedroom Caribbean Vacation Home

Mango Delight - 3 bedroom Caribbean Vacation Home

New Castle Village, St. James Parish Nevis
When you stay at this vacation home in Newcastle, you'll be near the airport, within a 5-minute drive of Cottle Church and Cat Ghaut Chip 'n Putt.
Opens in a new windowMango Delight - 3 bedroom Caribbean Vacation Home
Don't see what you're looking for?
See all available properties in Saint James Windward Parish
View all properties
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.

More ways to explore Saint James Windward Parish

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.