Windward Apartments, Estates and cottages

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North America Holidays
178660 properties
Caribbean Holidays
29002 properties
Pointe Milou
41 properties
Vitet
30 properties
Morne Criquet
26 properties
Marigot
18 properties
Gites Lorient
14 properties
Mont Jean
12 properties
Camaruche
10 properties
Petite Saline
7 properties

Windward

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157 Holiday homes

4

Holiday villa in Windward

Windward / Mont Jean

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
Villa Alphane is located on the estate of villa Arrowmarine in Mont Jean.This separate brand new bungalow is perfectly e..  …see more

from £300 / night

£2100 / week

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from £300 / night

19

Holiday villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Abby ABB is a very private and sensational villa set high in Vitet, St Barts. Abby offers guests some of St. Barth..  …see more

from £840 / night

£5880 - £11700 / week

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from £840 / night

18

Windward holiday villa rental

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our favourites villas One of our biggest villas One of the nicest pools of the islandThe villa Valentina is locat..  …see more

from £3172 / night

£22200 / week

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from £3172 / night

19

Holiday villa in Vitet

Windward / Vitet

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our favourites villas One of our villas the most private One of our spacious villasThe villa quotVinaquot is situ..  …see more

from £3120 / night

£21840 / week

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from £3120 / night

13

Holiday villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our two bedroom villas the most requested a perfect villa for honeymooners Villa Indonesia is located in Point..  …see more

from £1060 / night

£7416 / week

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from £1060 / night

14

Holiday villa in Windward

Windward / Lorient

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
A very private villa A maximum of sun Hilly House is a very private villa which dominates the view on Lorient and the is..  …see more

from £386 / night

£2700 / week

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from £386 / night

20

Windward holiday villa rental

Windward / Pointe Milou

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bon Temps BTR Built in Palladianstyle adapted to the tropics, Bon Temps BTR is a six bedroom villa located on the west s..  …see more

from £2143 / night

£15000 / week

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from £2143 / night

13

Holiday villa in Windward

Windward / Petite Saline

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Casa Zenial is a perfect villa for sophisticated customersThis Balinese villa is hidden at few minutes of the beach of S..  …see more

from £1715 / night

£12000 / week

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from £1715 / night

20

Villa rental in Marigot

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Florence is a roomy villa located on the hillside of Marigot.The villa has a spacious living and onto a terrace and the ocean view.The large pool is located between the living and the master bedroom.The second bedroom is connected to the living room.  …see more

from £1629 / night

£11400 / week

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from £1629 / night

20

Holiday villa rental

Windward / Camaruche

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Located on the hillside of Camaruche,Agave is one of the most private villas offering one of the greatest views of the i..  …see more

from £2143 / night

£15000 / week

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from £2143 / night

10

Windward holiday villa rental

Windward / Lorient

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The villa Escape is located in Lorient, at few steps away from the beach. The pool and the Jacuzzi are surrounded by a d..  …see more

from £1286 / night

£9000 / week

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from £1286 / night

17

Holiday villa in Windward

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Capri is one of our favourites villasLocated on the sunny side of Pointe Milou, facing the sunset, overlooking the tur..  …see more

from £1200 / night

£8400 / week

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from £1200 / night

20

Holiday villa in Windward

Windward / Petite Saline

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Dunes is certainly the most spectacular villa in StBarts With its 16,000 sq. ft new property, villa Dunes will sed..  …see more

from £12000 / night

£84000 / week

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from £12000 / night

21

Holiday home in Vitet

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
KAM named villa Amelie perched on the Marigot hillside offers a splendid view over Marigot bay. It features two bedrooms, two bathrooms, a solar heated pool and a heated Jacuzzi.This lovely villa has a charming character thanks to a chic and ethnic style mixed with ...  …see more

from £788 / night

£5512 / week

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from £788 / night

13

Holiday villa in Pointe Milou

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa quotZionquot is located in the sunset side of la quotPointe Milouquot.It is a brand new villa who combine all the..  …see more

from £858 / night

£6000 / week

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from £858 / night

20

Holiday villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach Marigot, LorientGustavia 15 min.Restaurant 10 min.Supermarket 10 min.Airport 10 min.  …see more

from £1715 / night

£12000 / week

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from £1715 / night

20

Villa rental in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
quotAu Ventquot is an exclusive property overhanging the cliff in Pointe Milou.You will be stunned by the panoramic view..  …see more

from £2143 / night

£15000 / week

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from £2143 / night

20

Holiday villa with swimming pool in Camaruche

Windward / Camaruche

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magnificently situated, Hill House BOW commands views of St Jean and beyond to St Martin. From the private terraces, the..  …see more

Pricing unknown

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Pricing unknown

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Carette CAR is a very private and spectacular villa with a large pool and excellent views of Lorient, St Barts. Bedro..  …see more

from £489 / night

£3420 / week

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from £489 / night

24

Holiday home in Windward

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
Located in the apartment complex of Les Terrasses on the hillside of St. Jean, ARD offers a wonderful view of the bay of St. Jean, convenience to the shops and restaurants in St. Jean Village, and the enjoyment of the large communal pool and sun deck. This one-bedroo...  …see more

from £411 / night

£2875 / week

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from £411 / night

20

Windward holiday villa rental

Windward / Vitet

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
There is a resident cat on this property.Villa Bibi BIB is perfection in every detail. Located high in Vitet, St Barts,..  …see more

from £1158 / night

£8100 - £17400 / week

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from £1158 / night

16

Holiday villa in Marigot

Windward / Marigot

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Captiva property is a located in Marigot at the edge of the sea. It is composed by the villas Captiva and Sea DreamThe..  …see more

from £3086 / night

£21600 / week

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from £3086 / night

20

Vitet holiday villa rental

Windward / Vitet

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
A new beautiful contemporary villa is built on a very private place on VitetLocated on a flat piece of land, manicured l..  …see more

from £3943 / night

£27600 / week

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from £3943 / night

20

Holiday villa in Lorient

Windward / Lorient

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
quotPalm Beachquot belongs to an owner who has a passion for the impressive villasLocated close to Lorient beach, at few..  …see more

from £12000 / night

£84000 / week

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from £12000 / night

6

Holiday villa in Windward

Windward / Pointe Milou

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Villa Papillon Blanc is located on the hillside of La Pointe Milou.This villa has two bedrooms which have a very nice ocean view.The pool is surrounded by an open living room and a terrace.The villa is close to the restaurant of the Christopher Hotel.  …see more

from £326 / night

£2280 / week

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from £326 / night

16

Villa accommodation in Windward

Windward / Petite Saline

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
quotMapouquot is a villa perched on the heights of Petite Saline, near Lorient.The villa has a magnificent view on the o..  …see more

from £2058 / night

£14400 / week

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from £2058 / night

20

Windward holiday villa rental

Windward / Pointe Milou

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
QuotLinquot is a villa located in Pointe Milou, surrounded by a large garden, with an ocean view toward the sunset. This 03 bedroom villa is perfect for the affordable budget.The living room is open onto a terrace with a nice ocean view.  …see more

from £386 / night

£2700 / week

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from £386 / night

8

Holiday villa with swimming pool in Camaruche

Windward / Camaruche

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Kokono VKA is nestled in the hillside of Camaruche and offers a beautiful view over Lorient bay and the surroundin..  …see more

from £849 / night

£5940 - £12000 / week

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from £849 / night

18

Windward holiday villa rental

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
St Barts Villa Heloa is a villa situated on the heights of the Pointe Milou. Due to its situation, the villa benefits fr..  …see more

from £1115 / night

£7800 / week

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from £1115 / night

20

Windward holiday villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
This manicured tropical paradise is an exclusive and perfect hideaway located on an unspoiled piece of land of 2 acre.Su..  …see more

from £2143 / night

£15000 / week

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from £2143 / night

24

Holiday home in Morne Criquet

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
Villa Sous la Falaise (SOU) is nestled just above the water at the eastern end of St. Jean Beach. Separate cottages offer a superb view of the white-sand beach, the bay, and the islets farther off the coast. This private and well-situated villa is within easy walking...  …see more

from £844 / night

£5906 / week

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from £844 / night

20

Villa rental in Windward with swimming pool

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Festival BEN is a very private and spectacular villa situated on Pointe Milou. There is a infinity pool with large..  …see more

from £1158 / night

£8100 - £11400 / week

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from £1158 / night

18

Holiday villa in Vitet

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
quotCasa Azulquot has a superb ocean viewThis renovation project villa is located on the top of Vitet and has a panorami..  …see more

from £1158 / night

£8100 / week

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from £1158 / night

24

Windward holiday home let

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
Villa Luz was built with privacy and relaxation in mind. Perfect for families and groups of friends, it is built on three different levels with views over beautiful Lorient Bay. A large built-in BBQ and dining area is perfect for entertaining at lunch or dinner. Gorg...  …see more

from £619 / night

£4331 / week

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from £619 / night

20

Holiday villa with swimming pool in Mont Jean

Windward / Mont Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Om AOM is located in the exclusive private gated community of Mont Jean on the north side of the island. The impre..  …see more

from £3858 / night

£27000 / week

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from £3858 / night

24

Holiday home in Morne Criquet

Windward / Morne Criquet

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
Light and bright, wide open interior spaces and a large and uniquely shaped pool make Villa MEL perfect for kids or for anyone who feels like smiling and having fun. Surrounded by royal palms and drenched in sun all day long, this home is the kind of villa that famil...  …see more

from £844 / night

£5906 / week

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from £844 / night

16

Mont Jean holiday villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Armor is a villa located in the private estate of Montjean, close to Pointe Milou area.Built at the top of the hill, th..  …see more

from £2400 / night

£16800 / week

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from £2400 / night