Holiday Rentals in Leeward

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Leeward

Villa Rosebud, 2BR, 2BA, (Sleeps 2-4), on the beach of Anse Des Cayes
9.8 out of 10, Exceptional, (45)
"Great location and place to stay. The villa has everything you could want and the property manager is super responsive. My wife and I really enjoyed our stay and would definitely stay again. "
United States
Michael S.
Villa Rosebud, 2BR, 2BA, (Sleeps 2-4), on the beach of Anse Des Cayes
Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool
10.0 out of 10, Exceptional, (2)
"Loved our 10 days in St. Barths. Villa Rose des Cayes was the perfect home base to explore the beaches, visit the towns and go shopping. It's a beautiful house, fully equipped in a quiet yet central location. The owner is very nice. He met us at the airport and was available to address any issue."
United States
Marcus P.
Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool
Luxury villa with magnificent sea view
10.0 out of 10, Exceptional, (26)
"Really enjoyed this villa. Great location, very nice layout, and very well kept. Add to that the extremely kind people that are taking care of you and you end up with a great vacation! "
United States
Colin M.
Luxury villa with magnificent sea view
🏝REAL BEACH VILLA ON THE BEACH !🏝CLOSE TO FLAMANS-ST JEAN BEACH CITY.REST.BARS
10.0 out of 10, Exceptional, (82)
"Great villa in an amazing location on the beach."
United States
Steve S.
🏝REAL BEACH VILLA ON THE BEACH !🏝CLOSE TO FLAMANS-ST JEAN BEACH CITY.REST.BARS
OPEN FOR NEW YEARS EVE... HOLIDAYS DEC. 28-JAN O3 DEPART...CONTACT ME FOR RATE!!
10.0 out of 10, Exceptional, (66)
"We loved our stay at Villa Alexi. Our favorite part was the pool and the incredible views. The home is well appointed and included many unexpected necessities like spices, coffee, tea, cooking supplies, soaps, toiletries, etc. we felt right at home and were treated so kindly by the owner Byron and the property caretaker Olivia."
United States
Stephen
OPEN FOR NEW YEARS EVE... HOLIDAYS DEC. 28-JAN O3 DEPART...CONTACT ME FOR RATE!!
Villa Vue mer Panoramique, à 5 Minute de la Plage !
9.8 out of 10, Exceptional, (6)
"Wonderful stay! "
United States
Tara T.
Villa Vue mer Panoramique, à 5 Minute de la Plage !
Saint Barths: brand new, luxury, architect-designed villa
10.0 out of 10, Exceptional, (22)
"Very nice, solidly constructed, very well appointed, great view and pool. Spacious, perfect for four. Would come back again."
United States
david G.
Saint Barths: brand new, luxury, architect-designed villa
Villa - Le Nid de Corossol 🐦 overlooking the Caribbean Sea 🏝️☀️
Villa - Le Nid de Corossol 🐦 overlooking the Caribbean Sea 🏝️☀️
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
10.0 out of 10, Exceptional, (5)
"Fabulous stay at a lovely villa with a great host, who made everything comfortable and seamless including assistance with a rental car and providing some great insights into the island. Would certainly stay again. "
United States
Vincent D.
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
On the Beach, in Saint Barth... Villa Mellow Mood
10.0 out of 10, Exceptional, (5)
"Great location! Beautiful sunsets over the harbor.. clean villa I will definitely be back!"
United States
shelly w.
On the Beach, in Saint Barth... Villa Mellow Mood
Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
10.0 out of 10, Exceptional, (4)
"Very good location "
United States
Parissa
Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY
10.0 out of 10, Exceptional, (10)
"We had a wonderful stay at this beautiful place on the beach. Joce was very friendly and helpful - he even drove some of us to the airport when we couldn't fit all of our bags in the car. The place is so relaxing and beautiful, we had trouble leaving even to see other parts of the island."
United States
Todd G.
🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY
SUNSET VILLA ANGEL ****
10.0 out of 10, Exceptional, (13)
"Great View and modern property. Private pool and large deck area. Car is a must for this location."
United States
Joseph B.
SUNSET VILLA ANGEL ****
Villa VOGUE - Panoramic Ocean View - St Jean
10.0 out of 10, Exceptional, (20)
"This is our 3rd time to the island, we previously stayed at Cheval Blanc but wanted to try out a villa. We could not have had a better experience. Sarah was amazing and communicating all details, Nicolas helped us on the spot when we could not find the house in our Moke. Villa Vogue is beautiful, well decorated, clean, each room has privacy. The view is unmatched. Sarah gives us a recommendation for Chef Julie who was outstanding. We will absolutely return."
United States
Rekha K.
Villa VOGUE - Panoramic Ocean View - St Jean
Charming lodges in st barth la pinta
Charming lodges in st barth la pinta
Villa Cinnamon sunset and sea view
Villa Cinnamon sunset and sea view
IXORA VILLA ST. BARTH
9.6 out of 10, Exceptional, (22)
"Very comfortable, clean and well outfitted for a couple to enjoy the island on a reasonable budget!"
United States
andrew L.
IXORA VILLA ST. BARTH
ASIAN PEARL by WIMCO St. Barth Properties
10.0 out of 10, Exceptional, (2)
"Amazing !! "
United States
Guillaume d.
ASIAN PEARL by WIMCO St. Barth Properties
Villa King Gustaf
Villa King Gustaf
Unique style loft, With spa-150 mètres to the beach
10.0 out of 10, Exceptional, (18)
"Wonderful property and host! the loft was perfect and had everything you could need - including snorkels and masks, umbrellas and chairs for the beach. A speaker to play music and a backgammon board and all kitchen utensils and coffee items. The deck and jacuzzi made the loft - such a beautiful setting and quiet too. Perfect location - safe and convenient to town and beach. Rudy our host was there at a moments notice and friendly and polite. "
United States
Sara B.
Unique style loft, With spa-150 mètres to the beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Leeward Hotel Reviews

Find out more about Leeward

Holiday Homes in Leeward

Search for holiday homes in Leeward on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Leeward using one of the methods below: 

  • View our selection of featured holiday homes in Leeward
  • Use the map to find apartments and other holiday rentals in the Leeward neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Leeward while they last

Look no further and take a look at our great range of rental properties in Leeward!