50 Best Vacation Rentals in Windward - Holiday Lettings - Cabins

Close

View larger map

Also consider

Pointe Milou
41 properties
Vitet
30 properties
Morne Criquet
26 properties
Marigot
18 properties
Lorient
14 properties
Mont Jean
12 properties
Camaruche
10 properties
Petite Saline
7 properties

Windward

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

157 Vacation rentals

5

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $500 / night

$3000 - $12000 / week

Book View

from $500 / night

20

Vacation villa with swimming pool in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Parsifal PAF is a small new villa in the Carenage area of Pointe Milou, a few steps from the Christopher Hotel. This charming villa has one bedroom, one bathroom and a pool.The living area is very open and nicely decorated in a contemporary style with modern ameni  …see more

from $750 / night

$5250 - $8625 / week

Inquire View

from $750 / night

19

Vacation home in Windward

Windward / Morne Criquet

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Overlooking the bay of St. Jean, Villa Namaste (AUM) is spacious and comfortable with fabulous sunsets views. When you enter the house, on your right you find the large and open living area, nicely decorated with hardwood furniture and African art. The living room overl  …see more

from $528 / night

$3700 / week

Inquire View

from $528 / night

15

Vacation villa rental

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Adore ADR is simple beachfront villa under one roof in Lorient, St Barts. There is a great yard and easy access to the beach. There is a combination livingdining area with a counter separating the kitchen from the living room. The bedrooms are located off living a  …see more

from $472 / night

$3300 - $4200 / week

Inquire View

from $472 / night

14

Vacation villa in Windward

Windward / Marigot

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Kyody is located on the height of Marigot, overhang the lagoon of Grand Cul de Sac at few minutes from the beaches of Grand Cul de Sac and Marigot.Kyody is a very private and spacious villa.Our customers like in this villa the ocean view from almost all the rooms, the l  …see more

from $300 / night

$2100 / week

Inquire View

from $300 / night

12

Vacation villa rental

Windward / Marigot

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Sea Dream is located on the estate of villa Captiva in Marigot.This separate brand new bungalow is perfectly equipped and private from the main villa, with a separate entrance and parking.Sea Dream has a living room, a bedroom, a bathroom and an extra room for a child.T  …see more

from $724 / night

$5063 / week

Inquire View

from $724 / night

24

Vacation home rental

Windward / Morne Criquet

6 6 Min stay varies

  • 6 bedrooms
  • Sleeps 6
  • Min stay varies
Located on the hillside between Camaruche and Marigot, with a sprawling view over the countryside and ocean, Villa Eclipse (JNM) is luxurious and architecturally innovative. Its design is based on clear-cut straight lines and angles, combined with the extensive use of n  …see more

from $1571 / night

$11000 / week

Inquire View

from $1571 / night

24

Vacation home in Windward

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
Villa Reef Point (RFP) boasts one of the finest locations on the island. At the very farthest point of the end end of St. Jean Bay, Villa RFP looks down over the clear blue water and out over the curve of the white sand beach. Recently built and decorated in contemporar  …see more

from $1857 / night

$13000 / week

Inquire View

from $1857 / night

24

Vacation home in Vitet

Windward / Vitet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
The aptly named Villa Imagine looks out over a wide expanse of tropical sea and sky from near the crest of the hill over Marigot. This delightful home offers a rare blend of simplicity and style, with a layout that makes the most of a great location and tasteful furnish  …see more

from $1428 / night

$10000 / week

Inquire View

from $1428 / night

20

Windward Vacation villa rental

Windward / Vitet

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
Soleimane is a brand new villa located on Vitet hillside.This elegant contemporary villa has a panoramic ocean view. The owner which is an architect has successfully combined the contemporary design with the exotic wood. The villa has all the assets for a perfect stay  …see more

from $804 / night

$5625 / week

Inquire View

from $804 / night

14

Pointe Milou Vacation villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa BBE is a charming one bedroom villa that can be rented individually or can be combined with the adjacent Villa Caramba for the convenience of an additional 2 bedrooms both linked by a path through gardens. The living and bedroom areas share the same room with a pa  …see more

from $386 / night

$2700 - $5250 / week

Inquire View

from $386 / night

24

Home rental in Windward

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
The stone path at the entryway to Villa Hill House (BOW) leads to a choice: On your right, a jaw-dropping view of the Atlantic, the islands of Tintamarre and Anguilla visible in the distance. On your left, a home so inviting and elegant that it rivals the natural beauty  …see more

from $2142 / night

$15000 / week

Inquire View

from $2142 / night

10

Vacation home in Windward

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
On a lush hillside overlooking Marigot Bay and its lovely beach, Villa Case et Cuisine blends island comfort with casual sophistication and provides a perfect vacation retreat for couples or families with children. The main terrace with its teak table and chairs is idea  …see more

from $342 / night

$2400 / week

Inquire View

from $342 / night

20

Vacation villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Cocoland is located in one of the best spot of the island La Pointe Milou.This colonial style villa has a wonderful ocean view. The villa has a lot of assets like the ocean view, the sunset view, and a perfect privacy.A large deck with a pool is overlooking the ocean an  …see more

from $1961 / night

$13725 / week

Inquire View

from $1961 / night

17

Vitet Vacation villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Les Mouttes PAY is a charming villa with heated pool, located in a private area in Vitet. With all of the rooms are under the same roof, it is a perfect family house.The spacious master bedroom is located on the first floor, with the other 2 small bedrooms located  …see more

from $450 / night

$3150 - $5250 / week

Inquire View

from $450 / night

24

Vacation home in Morne Criquet

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
Villa Vigie (GRE) is a wonderful villa perched on the cliff promontory over the east end of St. Jean Bay. The cozy and comfortable living area opens onto the terrace, pool and view. Conveniently located between Lorient and St. Jean village, Villa GRE is in close proximi  …see more

from $1142 / night

$8000 / week

Inquire View

from $1142 / night

12

Vacation villa in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Marigot is a small area on the eastern end of St Barts with a small beach. Marigot has some famous residents and is also close to Grand Cul de Sac which has several beach restaurants and watersports.BEDROOMView: Marigot beach Equipment: air conditioning,  …see more

from $1072 / night

$7500 / week

Inquire View

from $1072 / night

20

Vacation villa in Pointe Milou

Windward / Pointe Milou

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
An invitation to the total change of scenery and a call for total relaxation.An incomparable 180 ocean view and the sea just below. Seascape is a roomy brand new contemporary villa offering more than 7 000 sqf of living space... With exotic wood in profusion, a spaciou  …see more

from $11250 / night

$78750 / week

Inquire View

from $11250 / night

13

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $711 / night

$4977 - $23440 / week

Book View

from $711 / night

20

Pointe Milou Vacation villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Milou KID, located in Pointe Milou, has two bedrooms, two bathrooms and a pool. Stone steps lead to the villa that opens to a large living and dining area facing a spectacular view over the ocean and the surrounding islands. On the main level, to the left, a large  …see more

from $911 / night

$6375 - $10125 / week

Inquire View

from $911 / night

(2) Very Good 

18

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $575 / night

$4027 - $16456 / week

Book View

from $575 / night

20

Vacation villa rental

Windward / Camaruche

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
This spacious property offers an incomparable ocean view on the bay of Lorient, as well as on a multitude of Islands Fourchue, Bonhomme, Frgate, Saint Martin et Anguilla...The villa is located at a short drive two minutes from the beautiful beach of Lorient.Cumulus com  …see more

from $8347 / night

$58425 / week

Inquire View

from $8347 / night

9

Vacation villa with swimming pool in Windward

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Pastel EBA is a little gem, situated in the Vitet countryside with pastoral and ocean views. Simplistic in style, the villa has been constructed using modern materials such as wood, polished concrete, steel and glass, while at the same time keeping a traditional i  …see more

from $1233 / night

$8625 - $16500 / week

Inquire View

from $1233 / night

19

Vacation villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Seaweed SEA The ideas of Le Corbusier, Scarpa, Barragan and Mies Van der Rohe gave birth to the very first modern, contemporary, avantgarde villa on the island, just 10 years ago. Pure, minimalist lines harmonize perfectly with nature. Seaweed procures an unusual  …see more

Pricing unknown

Inquire View

Pricing unknown

24

Vacation home rental

Windward / Morne Criquet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
Surrounded by a garden of hibiscus, cactus, and flambouyant trees, Villa La Carette (CAR) is a place for a true tropical escapism. The colorful exterior and magnificent wide ocean view are balanced by a soothing interior decor of rattan, dark hardwoods, and smooth terra  …see more

from $607 / night

$4250 / week

Inquire View

from $607 / night

10

Camaruche Vacation villa rental

Windward / Camaruche

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Marisa VEL in Camaruche, St Barts, has been totally renovated and is truly spectacular. Very comfortable with harmonious colors and antique furniture. An extremely private villa with many areas for sitting in the shade or in the sun. The extensive gardens have som  …see more

from $686 / night

$4800 - $8250 / week

Inquire View

from $686 / night

15

Vacation villa in Vitet

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The beautiful Villa Anais AIA in Vitet, at the center of the eastern half of St. Barts, offers guests spectacular views of Grand Cul de Sac, Petit Cul de Sac, and St. Martin. Nestled high on a hillside facing north, the views, the warm Caribbean ambience, the sun and re  …see more

from $619 / night

$4332 - $7125 / week

Inquire View

from $619 / night

9

Petite Saline Vacation villa rental

Windward / Petite Saline

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa 21 is a villa located on the hillside of Lorient, close to Petite Saline.This very private villa has a stunned ocean view of Lorient Bay and the islands of quotFrgatequot, quotToc Vertquot and quotBonhommequot.BEDROOMView: Lorient bay Equipment: ai  …see more

from $986 / night

$6900 / week

Inquire View

from $986 / night

11

Windward Vacation villa rental

Windward / Petite Saline

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Harry is a brand new 2 bedroom, 2 bathroom villa located in Saline, overlooking the ocean and hillside area.This tastefully decorated villa features the living room, dining room, fully equipped kitchen, two bedrooms with its ensuite bathrooms, spacious terrace and  …see more

from $965 / night

$6750 / week

Inquire View

from $965 / night

33

Windward Vacation villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
- Are you looking for a place where to celebrate your love for a special someone?- Are you the kind of person who want the best they can get, not for boasting, but for their own, private enjoyment?Then, let the magic of BelAmour help your couple create lifelong  …see more

from $849 / night

$5943 - $13900 / week

Book View

from $849 / night

24

Vacation home in Windward

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
Villa Kyody (KDY) is a very attractive South American style villa located on the Marigot hillside. It has lovely views over all Grand Cul de Sac, Tortue Island and the ocean. Recently renovated both inside and outside. A pool and wooden deck blend in perfectly with the  …see more

from $371 / night

$2600 / week

Inquire View

from $371 / night

16

Vacation villa in Windward

Windward / Marigot

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
La Belle Epoque is located in Marigot at a walking distance from the beautiful Grand Cul de Sac lagoon, and the beach of Marchale. The public access to these beaches is by the beautiful garden of the hotel Guanahani close by. The villa is surrounded by a very nice tro  …see more

from $1050 / night

$7350 / week

Inquire View

from $1050 / night

18

Vacation home rental

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
Just a one-minute stroll from the white sands of St. Jean Beach, you will find Villa CAP among the palms, a quaint island bungalow that invites you to relax and dream of simpler times. Surrounded by flowering gardens, the ambiance of this villa is one of classic West In  …see more

from $200 / night

$1400 / week

Inquire View

from $200 / night

19

Marigot Vacation villa rental

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Blue Indies is a brand new villa ideally located within a walking distance to Marechale beach, a very private beach near the Guanahani Hotel and Spa. The lagoon of Grand Cul de Sac. The beach restaurant of the Guanahani Hotel. The tennis court of the Guanahani Hotel.Thi  …see more

from $4286 / night

$30000 / week

Inquire View

from $4286 / night

9

Vacation villa in Marigot

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Bougainvilliers is located hillside, at few steps from Marigot bay.This private villa has lovely views of Marigot Bay and the ocean.This two bedroom villa is perfect for a couple, or a family. The pool is surrounded by a terrace and the living room.Marigot Bay at a walk  …see more

from $879 / night

$6150 / week

Inquire View

from $879 / night

20

Vacation villa with swimming pool in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Caramba MBA is a delightful villa located at the end of Pt. Milou, with dramatic ocean views. It has been decorated with a wonderful use of both overstuffed wicker with white fabrics and mahogany beds with crisp white fabrics. The rooms are very bright and airy wi  …see more

from $836 / night

$5850 - $10500 / week

Inquire View

from $836 / night

12

Vacation villa accommodation

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Aliz dEden is located on the hillside of Pointe Milou.The villa has an ocean view of the ocean and the sunset.The living room and the two bedrooms open onto the pool and terrace, offering an ocean view from all rooms.BEDROOMView: Ocean Equipment: air con  …see more

from $600 / night

$4200 / week

Inquire View

from $600 / night

13

Vacation villa with swimming pool in Windward

Windward / Lorient

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Indigo Orchid TOR is a newly built and charming one bedroom villa in Lorient, St Barts that can be rented individually or can be combined with its neighbor villa, La Carette to make a total of 3 bedrooms. When rented separately, both villas maintain complete priva  …see more

from $450 / night

$3150 - $12375 / week

Inquire View

from $450 / night

12

Vacation villa in Lorient

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Les Jardins dEmmanuel EMM has two bedrooms, two bathrooms and a pool. Located in Lorient, this villa offers a spendid view over the ocean and the surrounding islands. This newly built villa is spacious and contemporary. It offers a large livingdining room that ope  …see more

from $804 / night

$5625 - $9000 / week

Inquire View

from $804 / night

20

Vacation villa in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Captain Cook is one of our largest villas. It is located in the private estate of La Pointe Milou. This large villa has an oversize living, with a large bar and a gourmet kitchen. Most of the bedrooms of this villa are composed by suites. The heated pool is like the vi  …see more

from $2679 / night

$18750 / week

Inquire View

from $2679 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page