Villas in Windward: Rent luxury villas in Windward

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  • St. Barts
  • St. Jean

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  • All locations
  • Pointe Milou (1)

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50 Holiday homes

Filters applied: Horse riding (1)

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 £345 / night

£2069 - £8276 / week

Book

from £345 / night

More results near

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 0.71 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 1.36 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 1.66 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 1.91 miles from Windward Show on Map

(1) Excellent 

1 / 46

Holiday villa with swimming pool in Colombier

St. Barts / Colombier

1 2 Min stay varies

Villa / 1 bedroom / sleeps 2 / Min stay varies

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from £268 / night

£2672 / week

Book

from £268 / night

Distance approx 1.92 miles from Windward Show on Map

1 / 8

Colombier holiday villa rental

St. Barts / Colombier

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

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from £764 / night

£4581 / week

Book

from £764 / 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 £325 / night

£2276 - £3718 / week

Book

from £325 / 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 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

Add to shortlist

from £96 / night

£649 - £894 / week

Book

from £96 / 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

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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 £483 / night

£2069 - £5311 / week

Book

from £483 / night

Distance approx 16 miles from Windward Show on Map

1 / 9

Holiday studio rental

Sint Maarten / Dawn Beach

2 5 nights min stay

Studio / sleeps 2 / 5 nights min stay

Add to shortlist

from £76 / night

£528 / week

Book

from £76 / 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 16.07 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 £242 / night

£1656 - £4483 / week

Book

from £242 / night

Distance approx 16.2 miles from Windward Show on Map

1 / 15

Dawn Beach holiday apartment rental

Sint Maarten / Dawn Beach

3 8 7 nights min stay

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

Add to shortlist

from £251 / night

£1756 / week

Book

from £251 / 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 16.53 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 17.19 miles from Windward Show on Map

1 / 7

Holiday studio with shared pool in Marigot, Saint Martin

Saint-Martin / Marigot, Saint Martin

2 7 nights min stay

Studio / sleeps 2 / 7 nights min stay

Add to shortlist

from £69 / night

£382 / week

Book

from £69 / night

Distance approx 17.85 miles from Windward Show on Map

1 / 27

Orient Bay holiday home rental

Saint-Martin / Orient Bay

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £128 / night

£891 - £2329 / week

Book

from £128 / night

Distance approx 17.85 miles from Windward Show on Map

(1) Excellent 

1 / 33

Orient Bay holiday villa rental

Saint-Martin / Orient Bay

2 5 5 nights min stay

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

Add to shortlist

from £180 / night

£1256 - £1661 / week

Book

from £180 / night

Distance approx 17.85 miles from Windward Show on Map

1 / 22

Home rental in Orient Bay

Saint-Martin / Orient Bay

2 4 7 nights min stay

House / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £182 / night

£1272 / week

Book

from £182 / night

Distance approx 17.87 miles from Windward Show on Map

(3) Excellent 

1 / 24

Cole Bay holiday apartment rental

Sint Maarten / Cole Bay

1 2 4 nights min stay

Apartment / 1 bedroom / sleeps 2 / 4 nights min stay

Add to shortlist

from £90 / night

£628 - £942 / week

Book

from £90 / night

Distance approx 17.88 miles from Windward Show on Map

(1) Excellent 

1 / 42

Orient Bay holiday home rental

Saint-Martin / Orient Bay

3 6 7 nights min stay

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

Add to shortlist

from £177 / night

£1233 - £2398 / week

Book

from £177 / night

Distance approx 17.95 miles from Windward Show on Map

1 / 18

Quartier D'Orleans holiday apartment rental

Saint-Martin / Quartier D'Orleans

2 4 5 nights min stay

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

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from £99 / night

£599 - £900 / week

Book

from £99 / night

Distance approx 17.95 miles from Windward Show on Map

1 / 21

Marigot, Saint Martin holiday apartment rental

Saint-Martin / Marigot, Saint Martin

3 6 5 nights min stay

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

Add to shortlist

from £149 / night

£900 - £1342 / week

Book

from £149 / night

Distance approx 17.98 miles from Windward Show on Map

1 / 16

Holiday apartment rental

Saint-Martin / Orient Bay

1 4 7 nights min stay

Apartment / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £99 / night

£688 - £825 / week

Book

from £99 / night

Distance approx 18.02 miles from Windward Show on Map

1 / 10

Holiday studio in Simpson Bay

Sint Maarten / Simpson Bay

4 3 nights min stay

Studio / sleeps 4 / 3 nights min stay

Add to shortlist

from £69 / night

£476 / week

Book

from £69 / night

Distance approx 18.02 miles from Windward Show on Map

1 / 21

Holiday villa in Orient Bay

Saint-Martin / Orient Bay

3 6 7 nights min stay

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

Add to shortlist

from £188 / night

£1306 - £3359 / week

Book

from £188 / night

Distance approx 18.03 miles from Windward Show on Map

1 / 33

Holiday home rental

Caribbean / St. Maarten - Saint Martin

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £410 / night

£2024 - £3155 / week

Book

from £410 / night

Distance approx 18.06 miles from Windward Show on Map

1 / 22

Holiday apartment with shared pool in Orient Bay

Saint-Martin / Orient Bay

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £99 / night

£688 - £840 / week

Book

from £99 / night

Distance approx 18.08 miles from Windward Show on Map

1 / 20

Orient Bay holiday apartment rental

Saint-Martin / Orient Bay

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £126 / night

£878 - £1031 / week

Book

from £126 / night

Distance approx 18.1 miles from Windward Show on Map

1 / 24

Home rental in Orient Bay with swimming pool

Saint-Martin / Orient Bay

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £146 / night

£1016 - £1756 / week

Book

from £146 / night

Distance approx 18.12 miles from Windward Show on Map

1 / 20

Holiday home in Orient Bay

Saint-Martin / Orient Bay

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £262 / night

£1833 - £3741 / week

Book

from £262 / night

Distance approx 18.13 miles from Windward Show on Map

1 / 46

Holiday villa in Orient Bay

Saint-Martin / Orient Bay

3 6 7 nights min stay

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

Add to shortlist

from £177 / night

£1233 - £2398 / week

Book

from £177 / night

Distance approx 18.15 miles from Windward Show on Map

1 / 15

Studio rental in Marigot with shared pool

Saint-Martin / Marigot

2 6 nights min stay

Studio / sleeps 2 / 6 nights min stay

Add to shortlist

from £86 / night

£548 / week

Book

from £86 / night

Distance approx 18.32 miles from Windward Show on Map

1 / 21

Orient Bay holiday villa rental

Saint-Martin / Orient Bay

3 6 7 nights min stay

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

Add to shortlist

from £273 / night

£1909 - £3665 / week

Book

from £273 / night

Distance approx 18.35 miles from Windward Show on Map

1 / 13

Holiday studio with shared pool in Oyster Pond

Saint-Martin / Oyster Pond

2 3 nights min stay

Studio / sleeps 2 / 3 nights min stay

Add to shortlist

from £39 / night

£268 - £375 / week

Book

from £39 / night

Distance approx 18.38 miles from Windward Show on Map

1 / 9

Holiday villa letting

Saint-Martin / Marigot, Saint Martin

5 10 3 nights min stay

Villa / 5 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £219 / night

£1527 - £1909 / week

Book

from £219 / night

Distance approx 18.41 miles from Windward Show on Map

1 / 26

Holiday villa with swimming pool in Orient Bay

Saint-Martin / Orient Bay

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £382 / night

£2672 - £6850 / week

Book

from £382 / night

Distance approx 18.47 miles from Windward Show on Map

1 / 23

Holiday studio in Marigot, Saint Martin

Saint-Martin / Marigot, Saint Martin

3 Min stay varies

Studio / sleeps 3 / Min stay varies

Add to shortlist

from £54 / night

£306 - £382 / week

Book

from £54 / night

Distance approx 18.53 miles from Windward Show on Map

1 / 21

Apartment rental in Orient Bay

Saint-Martin / Orient Bay

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £69 / night

£481 / week

Book

from £69 / night

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