Villas in Windward: Rent luxury villas in Windward

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  • St. Barts
  • St. Jean

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  • Pointe Milou (2)

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50 Holiday homes

Filters applied: Fishing (2)

1 / 33

Windward holiday villa rental

Windward / Pointe Milou

1 2 5 nights min stay

Villa / 1 bedroom / sleeps 2 / 5 nights min stay

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from £582 / night

£4071 - £6473 / week

Book

from £582 / night

1 / 5

Villa rental in Pointe Milou with swimming pool

Windward / Pointe Milou

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

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from £343 / night

£2055 - £8220 / week

Book

from £343 / night

More results near

Distance approx 0.34 miles from Windward Show on Map

(1) Very Good 

1 / 23

St. Jean holiday villa rental

St. Barts / St. Jean

3 6 7 nights min stay

Villa / 3 bedrooms / sleeps 6 / 7 nights min stay

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from £394 / night

£2759 - £4385 / week

Book

from £394 / night

Distance approx 0.37 miles from Windward Show on Map

1 / 24

Holiday villa rental

St. Barts / Gustavia

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £1957 / night

£13699 - £20548 / week

Enquire

from £1957 / night

Distance approx 0.43 miles from Windward Show on Map

1 / 24

Holiday villa rental

St. Barts / St. Jean

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £1077 / night

£7535 - £10274 / week

Enquire

from £1077 / night

Distance approx 0.44 miles from Windward Show on Map

1 / 17

Holiday villa with swimming pool in St. Jean

St. Barts / St. Jean

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £735 / night

£5137 / week

Enquire

from £735 / night

Distance approx 0.46 miles from Windward Show on Map

1 / 16

Holiday villa in St. Jean

St. Jean / St. Jean Beach

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £334 / night

£2335 - £3820 / week

Book

from £334 / night

Distance approx 0.47 miles from Windward Show on Map

1 / 24

Holiday villa rental

St. Barts / St. Jean

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £950 / night

£6644 - £10274 / week

Enquire

from £950 / night

Distance approx 0.68 miles from Windward Show on Map

1 / 15

Holiday villa rental

St. Barts / Grande Saline

2 6 Min stay varies

Villa / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £462 / night

£3228 / week

Book

from £462 / night

Distance approx 0.71 miles from Windward Show on Map

1 / 20

Holiday villa with swimming pool in Gustavia

St. Barts / Gustavia

1 2 Min stay varies

Villa / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £391 / night

£2733 / week

Book

from £391 / night

Distance approx 0.71 miles from Windward Show on Map

1 / 24

Villa rental in Gustavia with shared pool

St. Barts / Gustavia

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £391 / night

£2733 / week

Book

from £391 / night

Distance approx 0.71 miles from Windward Show on Map

1 / 26

Holiday villa rental

St. Barts / Gustavia

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £391 / night

£2733 / week

Book

from £391 / night

Distance approx 1.29 miles from Windward Show on Map

1 / 15

Holiday villa with swimming pool in St. Jean

St. Barts / St. Jean

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £637 / night

£4455 - £6507 / week

Enquire

from £637 / night

Distance approx 1.36 miles from Windward Show on Map

1 / 41

Holiday villa with swimming pool in Gustavia

St. Barts / Gustavia

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £713 / night

£4988 - £14251 / week

Book

from £713 / night

Distance approx 1.37 miles from Windward Show on Map

1 / 27

Anse des Cayes holiday villa rental

St. Barts / Anse des Cayes

2 4 5 nights min stay

Villa / 2 bedrooms / sleeps 4 / 5 nights min stay

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from £302 / night

£2100 / week

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from £302 / night

Distance approx 1.38 miles from Windward Show on Map

1 / 15

Apartment rental in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

Apartment / 3 bedrooms / sleeps 6 / Min stay varies

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from £560 / night

£3918 / week

Book

from £560 / night

Distance approx 1.64 miles from Windward Show on Map

(5) Excellent 

1 / 14

Holiday villa in Grand Cul-de-Sac

St. Barts / Grand Cul-de-Sac

4 8 7 nights min stay

Villa / 4 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £813 / night

£5685 - £8288 / week

Book

from £813 / night

Distance approx 1.66 miles from Windward Show on Map

1 / 18

Villa rental in St. Jean

St. Barts / St. Jean

2 5 4 nights min stay

Villa / 2 bedrooms / sleeps 5 / 4 nights min stay

Add to shortlist

from £214 / night

£1497 - £2352 / week

Book

from £214 / night

Distance approx 1.67 miles from Windward Show on Map

1 / 17

Holiday villa with swimming pool in Gustavia

St. Barts / Gustavia

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £411 / night

£2874 - £4915 / week

Enquire

from £411 / night

Distance approx 2 miles from Windward Show on Map

(1) Excellent 

1 / 15

Holiday villa rental

Anse des Flamands / Flamands Beach

3 5 Min stay varies

Villa / 3 bedrooms / sleeps 5 / Min stay varies

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from £480 / night

£3357 - £7535 / week

Book

from £480 / night

Distance approx 2.03 miles from Windward Show on Map

1 / 21

Holiday villa with shared pool in Anse des Flamands

St. Barts / Anse des Flamands

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £2466 / night

£17261 - £21816 / week

Enquire

from £2466 / night

Distance approx 2.13 miles from Windward Show on Map

1 / 24

Holiday villa rental

St. Barts / Lurin

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

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from £1224 / night

£8562 - £13357 / week

Enquire

from £1224 / night

Distance approx 2.23 miles from Windward Show on Map

(1) Excellent 

1 / 17

Holiday villa with swimming pool in Colombier

St. Barts / Colombier

1 2 5 nights min stay

Villa / 1 bedroom / sleeps 2 / 5 nights min stay

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from £322 / night

£2261 - £3692 / week

Book

from £322 / night

Distance approx 2.25 miles from Windward Show on Map

1 / 12

Holiday villa with swimming pool in Colombier

St. Barts / Colombier

2 2 Min stay varies

Villa / 2 bedrooms / sleeps 2 / Min stay varies

Add to shortlist

from £328 / night

£2355 - £6107 / week

Book

from £328 / night

Distance approx 2.51 miles from Windward Show on Map

1 / 18

Holiday villa in Petit Cul de Sac

St. Barts / Petit Cul de Sac

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

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Pricing unknown

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Pricing unknown

Distance approx 2.58 miles from Windward Show on Map

1 / 23

Holiday villa rental

St. Barts / Colombier

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

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from £1224 / night

£8562 / week

Enquire

from £1224 / night

Distance approx 15.59 miles from Windward Show on Map

(1) Excellent 

1 / 20

Orient Bay holiday condo rental

Saint-Martin / Orient Bay

2 5 5 nights min stay

Condo / 2 bedrooms / sleeps 5 / 5 nights min stay

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from £96 / night

£649 - £894 / week

Book

from £96 / night

Distance approx 15.64 miles from Windward Show on Map

(2) Excellent 

1 / 28

Philipsburg holiday apartment rental

Sint Maarten / Philipsburg

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

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from £52 / night

£340 - £408 / week

Book

from £52 / night

Distance approx 15.88 miles from Windward Show on Map

1 / 9

Holiday condo with shared pool in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min stay

Condo / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £294 / night

£2055 - £2398 / week

Book

from £294 / night

Distance approx 15.92 miles from Windward Show on Map

(4) Excellent 

1 / 18

Holiday villa with shared pool in Guana Bay

Sint Maarten / Guana Bay

2 5 7 nights min stay

Villa / 2 bedrooms / sleeps 5 / 7 nights min stay

Add to shortlist

from £189 / night

£1713 - £2432 / week

Book

from £189 / night

Distance approx 15.94 miles from Windward Show on Map

1 / 15

Holiday villa with swimming pool in Dawn Beach

Sint Maarten / Dawn Beach

3 8 5 nights min stay

Villa / 3 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £480 / night

£2055 - £5274 / week

Book

from £480 / night

Distance approx 15.95 miles from Windward Show on Map

1 / 12

Holiday condo rental

Sint Maarten / Dawn Beach

3 8 7 nights min stay

Condo / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £490 / night

£3425 / week

Book

from £490 / night

Distance approx 15.99 miles from Windward Show on Map

1 / 15

Holiday apartment with shared pool, golf nearby in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £343 / night

£2398 / week

Book

from £343 / night

Distance approx 16 miles from Windward Show on Map

1 / 16

Holiday apartment rental

Saint-Martin / Oyster Pond

3 8 7 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £168 / night

£1176 / week

Book

from £168 / night

Distance approx 16.04 miles from Windward Show on Map

1 / 22

Oyster Pond holiday apartment rental

Saint-Martin / Oyster Pond

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £61 / night

£427 / week

Book

from £61 / night

Distance approx 16.04 miles from Windward Show on Map

1 / 10

Apartment rental in Dawn Beach with shared pool

Sint Maarten / Dawn Beach

3 8 6 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 6 nights min stay

Add to shortlist

from £420 / night

£2672 / week

Book

from £420 / night

Distance approx 16.06 miles from Windward Show on Map

(1) Excellent 

1 / 16

Holiday condo rental

Saint-Martin / Oyster Pond

3 8 7 nights min stay

Condo / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £392 / night

£2740 - £3425 / week

Book

from £392 / night

Distance approx 16.07 miles from Windward Show on Map

1 / 19

Holiday condo in Dawn Beach

Sint Maarten / Dawn Beach

3 8 7 nights min stay

Condo / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £372 / night

£2603 / week

Book

from £372 / night

Distance approx 16.16 miles from Windward Show on Map

(1) Excellent 

1 / 46

Holiday villa with indoor pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £240 / night

£1644 - £4453 / week

Book

from £240 / night

Distance approx 16.32 miles from Windward Show on Map

(1) Very Good 

1 / 10

Philipsburg holiday apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £343 / night

£2398 / week

Book

from £343 / night

Distance approx 16.35 miles from Windward Show on Map

(1) Excellent 

1 / 19

Oyster Pond holiday villa rental

Saint-Martin / Oyster Pond

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £329 / night

£1966 / week

Book

from £329 / night

Distance approx 16.36 miles from Windward Show on Map

1 / 24

Holiday condo in Oyster Pond

Saint-Martin / Oyster Pond

3 6 7 nights min stay

Condo / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £255 / night

£1781 - £2294 / week

Book

from £255 / night

Distance approx 16.37 miles from Windward Show on Map

1 / 10

Ski hotel apartment to rent in Oyster Pond

Saint-Martin / Oyster Pond

1 2 Min stay varies

Hotel apartment / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £131 / night

£917 / week

Book

from £131 / night

Distance approx 16.42 miles from Windward Show on Map

1 / 9

Holiday apartment in Oyster Pond

Saint-Martin / Oyster Pond

3 8 6 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 6 nights min stay

Add to shortlist

from £459 / night

£3054 / week

Book

from £459 / night

Distance approx 16.43 miles from Windward Show on Map

1 / 15

Holiday home with swimming pool in Oyster Pond

Saint-Martin / Oyster Pond

3 6 7 nights min stay

House / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £197 / night

£1375 - £1527 / week

Book

from £197 / night

Distance approx 16.47 miles from Windward Show on Map

1 / 17

Holiday apartment in Oyster Pond

Saint-Martin / Oyster Pond

3 8 7 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £142 / night

£993 / week

Book

from £142 / night

Distance approx 16.48 miles from Windward Show on Map

(1) Excellent 

1 / 21

Holiday apartment rental

Sint Maarten / Philipsburg

1 2 1 night min stay

Apartment / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £48 / night

£302 / week

Book

from £48 / night

Distance approx 16.53 miles from Windward Show on Map

(1) Very Good 

1 / 34

Oyster Pond holiday apartment rental

Saint-Martin / Oyster Pond

3 8 7 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £236 / night

£1649 / week

Book

from £236 / night

Distance approx 16.53 miles from Windward Show on Map

1 / 18

Ski apartment to rent in Philipsburg

Sint Maarten / Philipsburg

3 8 4 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £174 / night

£2668 - £3151 / week

Book

from £174 / night

Distance approx 17 miles from Windward Show on Map

(1) Excellent 

1 / 23

Villa rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

2 6 3 nights min stay

Villa / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £154 / night

£1074 - £1851 / week

Book

from £154 / night

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