List your home
Apply filters
£ to

261 Holiday homes in Leeward

Reset search

Show results on map

Also consider

Luxury Villas
2,684 properties
Coastal Cottages
222 properties
Pet Friendly Cottages
27,095 properties
Romantic Breaks
3,207 properties
Group Holidays
17,143 properties
Log Cabin Holidays
238 properties
Rural Retreats
12,438 properties
City Breaks
8,475 properties
Holiday Cottages
17,239 properties
Villas in Spain
11,248 properties
Villas in Tenerife
707 properties
Gites in France
8,131 properties
Holiday Cottages in Cornwall
2,983 properties
London Holiday Apartments
941 properties
Florida Villas
905 properties
Villas in Ibiza
349 properties
Villas in Portugal
4,126 properties
Villas in Turkey
2,202 properties
Villas in Malta
455 properties
Lake District Cottages
940 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
261 Results  |  
15 Photos

Villa | 3 Bedrooms | sleeps 5

5 Nights min stay

Add to shortlist

from £461 /night

£3227 - £14485 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Triagoz is situated at 200 yards from popular Flamands Beach, close to Cheval Blanc Isle-de-France Hotel***** and Taïwana Hotel. A car is provided free from a Rent-a-Car company (Suzuki-Jimny).  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 4

6 Nights min stay

Add to shortlist

from £284 /night

£1988 - £5901 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Villa Adamas is a spectacular brand new 2-bedroom villa perfectly located on the hillsides of St Jean.  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £333 /night

£2330 - £6212 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Located on the hillside of Saline, this brand new 2-bedroom villa is the perfect choice for a quiet yet conveniently located place.  …see more

Featured properties

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £355 /night

£2485 - £7454 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Ideally located in the hillsides of Gustavia, Villa Harbour Light, recently built, is a stylish and modern villa that features 2 spacious bedrooms.  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £231 /night

£1615 - £7019 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Ylang Ylang is a charming and comfortable 2 bedroom villa located on the hillsides of Flamands, that has a great view on the sea.  …see more

10 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £98 /night

£684 - £1696 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Imaya is a brand new 1 bedroom villa conveniently located near the beautiful beach of Flamands  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £267 /night

£1864 - £6212 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Conveniently located in St Jean, Villa Akaroa is a brand new and luxurious 3 bedroom villa with a very nice sea view over St Jean Bay and the famous Eden Rock.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £1775 /night

£12423 - £29193 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
You're looking for an exceptionnal property to spend your next vacation in St Barts? You've definitely found it!  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £320 /night

£2237 - £7454 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Fleur de Cactus is a gorgeous 2 bedroom villa, with a beautiful view over the bay of St Jean, the ocean and the surrounding islands.  …see more

8 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £282 /night

£1969 - £10609 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Nestled in the hills overlooking Flamands, Villa White and Blue is a pretty and very quiet 4 bedroom villa that has a really great location  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £282 /night

£1973 - £5000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Ti Ylang is a very nice 1 bedroom villa with its private swimming pool and a large outdoor area.  …see more

19 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £160 /night

£1119 - £2609 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Natanya is a lovely 2 bedroom villa with a nice view over Flamands beach, one of the most beautiful beach of St Barth.  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £489 /night

£3417 - £9628 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Jasmin is ideally located in the hillsides of Lurin, very close to Gustavia and the gorgeous white sand beach of Gouverneur.  …see more

23 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £373 /night

£2609 - £9317 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Wastra (ROS) is a newly built, modern villa ideally located on the hillside of Gustavia, with a splendid view of the harbor and St Maarten. This villa offers the convenience of being downtown, but is still in a very private area. This villa is perfect for coupl...  …see more

30 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £444 /night

£3106 - £9007 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Art is a 3 bedroom villa with ocean views and is within walking distance to the beach. Art is a pleasant holiday villa rental ideally situated in the private estate of Roc Flamands in Flamands in St Barth in the French Caribbean.  …see more

40 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £178 /night

£1243 - £2174 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Letchi is a 1 bedroom villa surrounded by a beautiful tropical garden, has a large jacuzzi and is close to beaches and Gustavia.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £358 /night

£2504 - £7081 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Celina is a 2 bedroom villa located on Flamands beach.  …see more

28 Photos

Villa | 8 Bedrooms | sleeps 16

5 Nights min stay

Add to shortlist

from £1775 /night

£12423 - £37268 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Pointe is a large villa that is located within walking distance of restaurants, boutiques and Shell Beach.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £489 /night

£3417 - £9628 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
One of the largest two-bedroom villas on the island, Villa Shalimar (JBA) offers a great degree of privacy as well as wonderful views over the south coast of the island and across the Caribbean Sea. The Lurin location is also ideally located with easy access to both ...  …see more

32 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £932 /night

£6522 - £21740 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Rock U is a 3 bedroom villa with views of the ocean and sunset. It is just a short drive to the beach.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £364 /night

£2547 - £5901 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Adamas is a 2 bedroom villa which offers a panoramic view from its outdoor living area and has a pool that overlooks Saint Jean Bay. The outdoor living will allow you to admire the panoramic view of Saint Jean bay.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £524 /night

£3665 - £9317 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Micalao is a private 3 bedroom villa with an ocean view.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £2237 /night

£15653 - £33479 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Welcome to Flamands Beach Villa, a stunning villa located directly on the pristine, white sands of Baie de Flamands one of St. Barth's most beautiful beaches. • Board: Self Catering  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

7 Nights min stay

Add to shortlist

from £1953 /night

£13665 - £26087 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
From Villa Le phare's (LAM) prestigious position on the hillside above Gustavia, you can stand on your terrace and take in the spectacular views of the harbor, the quaint prettiness of Gustavia, the anchorage with an array of impressive yachts, and the most incredibl...  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £323 /night

£2261 - £11678 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Villa Ted is a 2 bed luxury villa located in the beautiful surroundings of Dévé in St Barths offering guests a beautiful terrace area with panoramic sea views. • Board: Self Catering  …see more

21 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £675 /night

£4721 - £20497 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa AMI offers its guests the ultimate in traditional Colonial charm. From high up in Lurin, this home looks out over the harbor of Gustavia and the Caribbean Sea beyond, a spectacular vista day and night. Furnished in true West Indies style, with hardwood four-pos...  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £249 /night

£1740 - £5591 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Villa Rosebud is a charming villa in Anse des Cayes, St Barth. Perfect for a honeymoon, Rosebud is just steps away from the Anse des Cayes beach by a little path through the garden.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £444 /night

£3106 - £10435 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Byzance is a 2 bedroom villa that offers calm and intimacy overlooking the ocean.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £284 /night

£1988 - £3914 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Mahogany is a private villa with ocean view and only steps from the beach.  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £1598 /night

£11181 - £18634 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The entrance to Villa Gouverneur Dream (OTO) leads conveniently into an impressive open-plan kitchen and dining area, but you will only pause there to set down your bags before heading straight out to the terrace. Take in the view down the lush hillside of poirier tr...  …see more

24 Photos

House | 4 Bedrooms | sleeps 5

5 Nights min stay

Add to shortlist

from £710 /night

£4969 - £20497 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
La Maison sur le Port (Villa MSP) provides a rare combination of the ultimate central location with unexpected spaciousness and high levels of luxury. Spend less of your St. Barth vacation behind the wheel of a car. Try the Gustavia townhouse lifestyle, without givin...  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £362 /night

£2531 - £3940 / week

View

Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car advised
  • No pets allowed
Cap Frehel is a 1 bedroom villa on the beach with access to tennis court on the property.  …see more

28 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £799 /night

£5591 - £16771 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Casaprima is a 3 bedroom villa with views of the ocean and the yachts anchored in the bay facing the villa.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £3993 /night

£27951 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Blue Swan offers ocean and sunset views. It has a large deck and swimming pool with a bar.  …see more

16 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £373 /night

£2609 - £4969 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Mahi (AHI) is a convenient and comfortable apartment tastefully decorated with modern furnishings. Set just on the harbor in the heart of Gustavia, Villa AHI offers a fantastic view of the yachts. The fully equipped kitchen opens onto the comfortable living and dinin...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £781 /night

£5466 - £27951 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Midway down the hill from Lurin to Plage de Gouverneur, Villa Gouverneur View (REF) offers an ideal location of which many a beach-goer has wistfully thought, "I wish I lived there." Step through the doorway and you are inside one of the finest examples of a classic ...  …see more

33 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £395 /night

£2764 - £5870 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Costa Nova is a 2 bedroom villa offering ocean and sunset views.  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £355 /night

£2485 - £6212 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Ô Pure (MLO)'s classic French West Indies design and beautifully landscaped gardens make it ideal for relaxing any time of day or night. A pool and terrace sheltered in an interior courtyard become the favored gathering place for families or friends staying in ...  …see more

14 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

Add to shortlist

from £196 /night

£1367 - £2796 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Located in the Colony Club complex in Gustavia, Apartment CCG lets guests enjoy St. Barth in a way that will be new to many: a convenient, in-town lifestyle combined with beautiful views and verdant gardens. Looking out over the harbor, CCG provides a fascinating vie...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £1376 /night

£9628 - £34162 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Arte is a 4 bedroom villa with ocean views, large heated pool and jacuzzi and air-conditioned fitness room.  …see more

15 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £551 /night

£3851 - £9628 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Zen is a luxury two bedroom villa located in the exclusive Pointe Milou area of St Barths. This romantic villa provides wonderful sea views and fantastic sunsets. • Board: Self Catering  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £1243 /night

£8696 - £12423 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Isabella is a lovely 4 bedroom villa with private pool and breathtaking panoramic views located on the hillside over looking Saint Jean Bay. • Board: Self Catering  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £977 /night

£6833 - £19876 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Welcome to Villa Ellena, a stunning and truly magical St Barths Villa rental. This luxury 3 bedroom villa is located midway between St. Jean and the village of Lorient and offers panoramic views over the turquoise St Jean Bay. • Board: Self Catering  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £710 /night

£4969 - £18634 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Ti Moun (MOU) is one of those rare properties that offers views so captivating that the beauty of the house almost goes overlooked. From a secluded Lurin hilltop high above the picturesque harbor of Gustavia, you will enjoy an unparalleled vista of the blue Car...  …see more

21 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £932 /night

£6522 - £21740 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The brand-new Villa Rock U (ROK) shows what smart design and good taste can achieve. While modern and practical, this home has true soul as well. The living area and terrace are open and spacious, stylishly decorated and offering a balance of sunlight and shade. With...  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £666 /night

£4659 - £15528 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Matajugai is a 2 bedroom villa with ocean views and is only a short walk to the beach.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £1953 /night

£13665 - £26087 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Lam is a 3 bedroom villa with ocean and sunset views and is within walking distance of shops and restaurants.  …see more

28 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £746 /night

£5218 - £15528 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Dasha is a 3 bedroom villa that offers privacy, comfort and beautiful ocean views.  …see more

24 Photos

House | 4 Bedrooms | sleeps 5

5 Nights min stay

Add to shortlist

from £435 /night

£3044 - £18634 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Habitation Saint Louis (HSL) is located on the hillside above the charming village of Corossol. Private and quiet, this villa offers you sunsets and a sea views of Corrosol and Gustavia Harbour entrance. This villa is built on two levels and offers private and direct...  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £3550 /night

£24845 - £27951 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
A townhouse in Gustavia, which is both colonial and modern, offering an incredible view of the sea: Welcome to Wickie (Villa WIK). This brand new property possesses two architectural styles, seemingly opposing in appearance and yet complementing one another in both f...  …see more